CN114105780B - Synthesis method of isooctylamine and derivative by one-pot method - Google Patents

Synthesis method of isooctylamine and derivative by one-pot method Download PDF

Info

Publication number
CN114105780B
CN114105780B CN202111581873.2A CN202111581873A CN114105780B CN 114105780 B CN114105780 B CN 114105780B CN 202111581873 A CN202111581873 A CN 202111581873A CN 114105780 B CN114105780 B CN 114105780B
Authority
CN
China
Prior art keywords
pressure
reaction
butyraldehyde
hydrogen
isooctylamine
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.)
Active
Application number
CN202111581873.2A
Other languages
Chinese (zh)
Other versions
CN114105780A (en
Inventor
郭华
王良
刘宇
寇功明
李春阳
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiayijia Biotech Inc
Original Assignee
Jiayijia Biotech Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Jiayijia Biotech Inc filed Critical Jiayijia Biotech Inc
Priority to CN202111581873.2A priority Critical patent/CN114105780B/en
Publication of CN114105780A publication Critical patent/CN114105780A/en
Application granted granted Critical
Publication of CN114105780B publication Critical patent/CN114105780B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/82—Purification; Separation; Stabilisation; Use of additives
    • C07C209/84—Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • 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
    • Y02P20/584—Recycling of catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The synthesis method of isooctylamine and derivatives by a one-pot method is technically characterized by comprising the following steps: step 1, adding n-butyraldehyde, skeleton nickel or skeleton copper or a mixture thereof and pure water washing liquid into a high-pressure reaction kettle, and stirring the reaction kettle at a constant speed of 500r/h under the nitrogen atmosphere of 0.2 MPa; step 2, reacting for 1h at the temperature of less than or equal to 25 ℃ under normal pressure, slowly heating to 35 ℃ and reacting for 0.5h, and rapidly cooling to below 35 ℃ in a cooling water environment; step 3, introducing liquid ammonia or dimethylamine, flushing hydrogen to raise the pressure to (and keep the pressure at) 3.0MPa, and increasing the stirring speed to 700r/h until the hydrogen is not absorbed any more, and ending; and step 4, rectifying and collecting fractions at 155-156 ℃. The method has the advantages of simple process, easy small scale mass production and the like.

Description

Synthesis method of isooctylamine and derivative by one-pot method
Technical Field
The invention relates to a synthesis method of organic amine, in particular to an amination reduction reaction of unsaturated aldehyde substances, and specifically relates to a synthesis method of isooctylamine and derivatives by a one-pot method.
Background
Isooctylamine is an excellent fine chemical raw material and is widely used in the fields of surfactants, fine chemical intermediates, dye raw materials and medical intermediates. For example, isooctylamine and succinic acid are added to prepare isooctyl iminosuccinic acid monosodium salt, acrylic acid is added to prepare N-carboxyethyl isooctyl amino sodium propionate, ethylene oxide is reacted to prepare ethanol gasoline additive N, N-dihydroxyethyl isooctylamine, N, N-dimethyl octylamine is reacted with 3-chloro-2-hydroxy sodium propane sulfonate to obtain low-foaming amphoteric surfactant, which is one of the known amphoteric surfactants with lower surface tension and has excellent performance.
Direct reductive amination (DRA, direct Reductive Amination) is the most practical method for synthesizing chiral amine medicaments at present, and C-N bonds can be constructed in one step. AH (AH)(Asymmetric Hydrogenation asymmetric hydrogenation) and DRA may share clean reductant H 2 The byproduct is only H2O, which is a green, economical and efficient method for synthesizing chiral amine compounds. Yuan Shuai of the university of northwest agriculture and forestry science and technology discloses that AH of C=C bonds and DRA of C=O bonds in alpha, beta-unsaturated aldehydes are successfully synthesized into a series of chiral secondary amines under the catalysis of Rh- (R) -Segphos in a one-pot method in the tandem method of asymmetric hydrogenation and direct reductive amination to synthesize the chiral secondary amines and antifungal activity of the chiral secondary amines. And specific process parameters of N,2, 3-triphenylpropylamine are listed in the abstract, wherein the hydrogen pressure is 50atm, the reaction temperature is 60 ℃, and the reaction time is 24 hours.
Since the purpose of the above study is to screen for chiral compounds, which have higher demands on the use of catalysts, a detailed description is given in page 19 of the paper, page 2-2, in which the metal Ir is cheaper but is not discarded given the enantiomeric excess, and the other 8 catalyst combinations use the metal Rh without exception, but the current commercial metal Rh offers fluctuate above 3000/g (gold screening data). It can be seen that the use of this process flow may be difficult to recover costs if considering catalyst loss issues, and therefore does not have an industrial prospect.
Other aldehyde reductive amination reactions, for example, with 2% of manganese as catalyst, with hydrogen and imine intermediates are also mentioned in 1.3.2 of the research background of the paper; chiral phosphoric acid is used as a catalyst, hans ester is used as a hydrogen source, and the chiral phosphoric acid reacts with aniline and aniline derivatives; with chiral Lewis base catalyst, with HSiCl 3 Is a hydrogen source, and reacts with aniline derivatives.
Chen Cuina, chemical report (2013), 76 (4) discloses that water is used as a solvent, 0.5% of liquid inorganic base (NaOH), solid inorganic base (such as metal oxides and hydrotalcite), or polyvinylpyrrolidone or solid organic base (such as alkaline resin with tertiary amine end group) are used as catalysts at normal pressure to catalyze the aldol condensation reaction of n-butyraldehyde to generate octenal (2-ethyl-2-hexenal), and the application of nickel and copper as catalysts to catalyze the condensation reaction is not disclosed.
Regarding framework metals, zhou Xiaojian, etc., in "influence of substituents on the benzene ring and alkylating agent alcohols on reduction-alkylation to N-alkylarylamines", university of Large Commission (1999), 39 (1) discloses the preparation of N-alkylarylamines by reductive alkylation of aromatic nitro compounds by framework nickel selective catalysis.
Regarding reductive amination reaction catalyzed by nickel, jianhui, etc., in activated carbon supported nano nickel catalytic glucose reductive amination reaction, chemical progress (2011), 30 (6) discloses catalytic preparation of meglumine crystals in a hydrogen atmosphere of 2.5MPa or 5.0MPa with activated carbon supported nano nickel (Ni/AC) as a catalyst. The particle size of the nano nickel is about 20 nm-30 nm.
Regarding the performance difference of nano nickel and skeleton nickel, chen Rizhi and the like in the comparison of catalytic performance of nano nickel and skeleton nickel, chemical engineering journal (2003), 54 (5) compare the nano nickel and the skeleton nickel in detail in nitrophenol hydrogenation reaction, and the skeleton nickel is a typical hydrogenation catalyst, and the skeleton nickel catalyst has the advantages of low price and the like, but researches find that the catalytic selectivity of the skeleton nickel is low. And is also relatively easy to deactivate. In the same reaction time, the yield of nano nickel is more than 2 times of that of skeleton nickel. Specific surface areas of the fresh nano nickel and the fresh skeleton nickel are 43.58m respectively 2 · g -1 ，71.18 m 2 · g -1 After recycling, the nano nickel can be subjected to agglomeration phenomenon, the particle size is increased, and the change of skeleton nickel is smaller.
In addition, in the prior art, organic amines can also be prepared by dehydration of alcohols with ammonia at elevated temperature and pressure. The method for synthesizing isooctylamine disclosed in the patent publication No. CN1250517C uses isooctyl alcohol as raw material and Cu-Co/Al 2 O 3 Diatomite is used as a catalyst, isooctanol is mixed and reacted with ammonia gas and hydrogen gas under the condition of 0.1-2.0 Mpa and 150-280 ℃, and finally about 66wt% of 2-ethylhexyl amine (final product), about 30wt% of 2-ethylhexanol and about 3.0wt% of byproducts are obtained. The preparation method of the catalyst is also disclosed in the technical proposal, and whether the catalyst can be used for the preparation or not is not disclosedWith other similar catalysts.
Disclosure of Invention
The invention aims to provide a synthesis method of isooctylamine and derivatives by a one-pot method, which fundamentally solves the problems, and has the advantages of simple process, easiness in small-scale mass production and the like. The raw material n-butyraldehyde is subjected to condensation reaction by alkaline framework nickel catalysis to obtain octenal, and the octenal is subjected to ammonification and hydrogenation to obtain the final product isooctylamine, which has lower reaction condition requirements.
In order to achieve the above purpose, the present invention provides the following technical solutions: the synthesis method of isooctylamine and derivatives by a one-pot method is technically characterized by comprising the following steps:
step 1, adding 100 parts by weight of n-butyraldehyde, 4-6 parts by weight of alkaline skeleton nickel or skeleton copper or a mixture thereof into a 500ml high-pressure reaction kettle, and stirring the reaction kettle at a constant speed of 500r/h under a nitrogen atmosphere after three times of nitrogen replacement under the pressure of 0.2 MPa; the weight ratio of the framework metal to the n-butyraldehyde is 1: 10-1: 100;
step 2, reacting for 1h at the temperature of less than or equal to 25 ℃ under normal pressure, slowly heating to 35 ℃ for 0.5h, slowly heating to 60 ℃ for 0.5h, slowly heating to 90 ℃ for 0.5h, and rapidly cooling to below 35 ℃ in a cooling water environment;
step 3, replacing three times by using 0.2MPa hydrogen, and introducing liquid ammonia or dimethylamine, wherein the feeding mole ratio of the liquid ammonia or dimethylamine to n-butyraldehyde is more than or equal to 0.55:1, charging hydrogen, boosting to 3.0MPa (and keeping), increasing the stirring speed to 700r/h, heating to 90 ℃ to activate the reaction, and after no more hydrogen is absorbed, keeping for 0.5h, and ending;
and 4, filtering the mother liquor, recovering the catalyst, evaporating ammonia gas at normal pressure, and rectifying and collecting the fraction at 155-156 ℃.
By step 3, the-c=o bond is converted to a-C-N bond, which may involve the following two sets of reactions in the mixed system:
+ R 3 NH 2 ===>/> A1
+ 2H 2 ===>/> A2
+ H 2 ===>/> B1
+ R 3 NH 2 ===>/> B2
in the above reaction formula, R 1 Mainly ethyl, R 2 Mainly methyl, R 3 Mainly hydrogen.
The invention has the beneficial effects that:
the whole synthesis process mainly comprises two stages: in the first stage, raw material n-butyraldehyde is selected, alkaline skeleton nickel or skeleton copper or a mixture thereof is used as a catalyst, and aldol condensation reaction is carried out in a gradually heating state under the nitrogen protection atmosphere. The second stage can be continued without extracting any reactant, the nitrogen protection atmosphere is replaced by high-pressure hydrogen protection atmosphere, ammonification and hydrogenation are carried out under the conditions of saturated ammonia (amine) and saturated hydrogen, and finally the product isooctylamine is obtained. The first stage and the second stage reactions can share the framework metal catalyst, and can directly perform two-stage reactions without additional raw materials or extraction of byproducts. The reaction condition is mild, the process is simpler and safer, and the by-product is only H 2 O, the production process is more environment-friendly.
In the first stage, n-butyraldehyde participates in the reaction in alpha and beta positions as much as possible by a gradual heating method, so that the generation of byproducts (such as polyacetal and disproportionation reaction) in a high-temperature environment is effectively reduced, octenal is generated by the n-butyraldehyde reaction as much as possible, and the yield of isooctylamine in the second stage reaction is improved. In two n-butyraldehyde molecules participating in the reaction, O and H at the alpha position of one n-butyraldehyde are activated, H at the beta position of the other n-butyraldehyde is activated, O and H at the alpha position are combined with H at the beta position to generate more stable product water, the reaction is promoted to be carried out in the forward direction, and the two n-butyraldehyde are condensed into octenal. In actual production, the raw material price of octenal is far higher than that of n-butyraldehyde, so that the synthesis of octenal by adopting a n-butyraldehyde one-pot method is a synthesis method with higher cost performance.
In the second stage, the ammonification and hydrogenation of aldehyde ketone is usually carried out by reacting saturated aldehyde or ketone with ammonia (or amine), the process condition is mild, and the method is suitable for the production of small-scale multi-variety series products, such as ammonification and hydrogenation of octenal and liquid ammonia to obtain octylamine, ammonification and hydrogenation of octenal and dimethylamine to obtain N-octyl dimethylamine, and the like. When the enal is hydrogenated by ammonification, the double bond of enamine and hydrocarbon is hydrogenated together, and the imine intermediate with higher activity is more prone to be obtained in a reaction mixed system, and the imine intermediate reacts with hydrogen to generate a more stable methylamine substrate.
In summary, the main improvements of the process of the present invention mainly include the following: the cheaper framework nickel or framework copper is selected to replace the expensive Rh- (R) -Segphos catalyst or nano nickel catalyst in the prior art, and the catalyst catalyzes the condensation of n-butyraldehyde on one hand and the hydrogenation and ammoniation of octenal on the other hand, so that the production cost of isooctylamine is effectively reduced. The copper-nickel-based catalyst is more suitable for the production and application of low-value mass chemical basic raw materials.
Detailed Description
The following describes the present invention in detail by way of specific examples. The synthesis method of isooctylamine and derivatives by a one-pot method mainly comprises the following reaction steps:
step 1, adding 100 parts by weight of n-butyraldehyde, 4-6 parts by weight of alkaline framework nickel or framework copper or a mixture thereof serving as a catalyst into a high-pressure reaction kettle, replacing three times with nitrogen at 0.2MPa, and stirring the reaction kettle at a constant speed of 500r/h under a nitrogen atmosphere; the weight ratio of the framework metal to the n-butyraldehyde is 1: 10-1: 100;
and 2, reacting for 1h at the temperature of less than or equal to 25 ℃ under normal pressure, slowly heating to 35 ℃ for 0.5h, slowly heating to 60 ℃ for 0.5h, slowly heating to 90 ℃ for 0.5h, and rapidly cooling to below 35 ℃ in a cooling water environment. The following aldol condensation reaction mainly occurs during the gradual temperature rise in this step.
+ /> ===> /> + H 2 O ①
Step 3, the condensation is completed without separation, hydrogen with the pressure of 0.2MPa is used for three times, liquid ammonia or dimethylamine is introduced, and the molar ratio of the liquid ammonia or dimethylamine to octenal is more than or equal to 1.1:1, namely excess liquid ammonia, charging hydrogen gas, raising the pressure to 3.0MPa (and keeping the pressure at about 30 atm), raising the stirring speed to 700r/h, raising the temperature to 90-100 ℃ to activate the reaction, monitoring in real time to avoid the increase of the alcohol content when the temperature is raised to be higher than 110 ℃ in the reaction process, and stopping the reaction process after the reaction is continued for about 0.5h after no more hydrogen is absorbed. This step mainly occurs as follows.
) Ammonification reaction:
+ NH 3 ===> /> + H 2 O ②
+ NH 3 ===> />+ H 2 O ③
3) Hydrogenation reaction:
+ 2H 2 ===> />④
+ H 2 ===> /> ⑤
the-C=O bond of the alpha position of octenal is finally replaced by the-C-N bond through ammonification and hydrogenation reaction.
In the reactions (2) - (5), carbon atoms at two ends of an unsaturated bond are activated in the process of heating to 90 ℃, and a large amount of negative electricity-NH and positive electricity free H+ exist in the reaction system, and the oxygen atoms of an acyl at the end are easier to be replaced compared with-NH, so that the free negative electricity-NH is replaced by negative electricity-OH which is easy to fall off, and the free negative electricity-OH is quickly combined with the free H+ to generate water, so that the reaction (2) is promoted to be carried out positively. Meanwhile, as the intermediate with unsaturated bond amine terminal in the reaction (2) is extremely active, the unsaturated bond thereof is immediately combined with free H+ to generate hydrogenation reaction after generation, and the intermediate participates in the reaction (3) only instantaneously, so that resolution description is carried out for convenience of explanation of the reaction principle.
In the reaction (3), the reaction kettle is in a high-pressure hydrogen atmosphere, namely, hydrogen is excessive, liquid ammonia with the mole number higher than that of octenal is added, the forward reaction is facilitated, and when the concentration of enamine intermediate in the reaction system is reduced, the forward reaction (2) is facilitated until all octenal participates in the reaction. Thus, it is possible to determine whether the reaction is complete by monitoring the amount of hydrogen. For example, the pressure threshold value can be set in a constant pressure mode, and when the pressure in the kettle body is lower than the threshold value, the air inlet valve of the hydrogen inlet pipeline is automatically opened. When the pressure in the reaction kettle is kept constant for a long time, the reaction is complete. Therefore, in actual production, the reaction end point can be monitored remotely by detecting the open-close state interval time of the air inlet valve.
And 4, filtering the mother liquor, recovering the catalyst, evaporating ammonia gas or dimethylamine gas at normal pressure, and rectifying and collecting the fraction at 155-156 ℃.
Example 1
Step 1, adding 100g of n-butyraldehyde (AR, 98 percent, shanghai Michelia biochemical technology), 4.5g of skeleton nickel and 100 parts by weight of pure water washing liquid with the pH value of 7.5-8 into a 500ml high-pressure reaction kettle, and carrying out nitrogen substitution for three times under the pressure of 0.2MPa, wherein the reaction kettle is stirred at a constant speed of 500r/h under the nitrogen atmosphere; the weight ratio of the framework metal to the n-butyraldehyde is 1: 10-1: 100;
and 2, reacting for 1h at the temperature of less than or equal to 25 ℃ under normal pressure, slowly heating to 35 ℃ for 0.5h, slowly heating to 60 ℃ for 0.5h, slowly heating to 90 ℃ for 0.5h, and rapidly cooling to below 35 ℃ in a cooling water environment. The following aldol condensation reaction mainly occurs in the gradual temperature rising process of the step, and the formation of polyacetal can be avoided by low-temperature condensation.
And 3, replacing three times with 0.2MPa hydrogen without separation after condensation is finished, introducing 15g (more than or equal to 99% of the Ruxi chemical industry) of liquid ammonia, introducing hydrogen to boost (and maintain) 3.0MPa, increasing the stirring speed to 700r/h, heating to 90 ℃ to activate the reaction, monitoring in real time to avoid the increase of the alcohol content when the temperature is increased to be more than 110 ℃, and stopping the reaction after the reaction is continued for about 0.5h after no more hydrogen is absorbed. This step mainly takes place as follows.
And step 4, filtering mother liquor, recovering a catalyst, evaporating ammonia gas at normal pressure, and rectifying and collecting a fraction at 155-156 ℃ to obtain the yield of 85.3%.
Example 2
The liquid ammonia in the step 3 is replaced by 40g (more than or equal to 99 percent) of dimethylamine, the Zibo Kai commercial Co., ltd.) and the step 4 is to distill dimethylamine gas, and the yield is 81.7 percent. Other reaction conditions were the same as in example 1.
Example 3
The skeletal nickel in the step 1 is replaced by a mixture of 3g of skeletal nickel and 1.5g of skeletal copper, and different manufacturers (Zibo Kai commercial Co., ltd.) are selected for the liquid ammonia (more than or equal to 99%) in the step 3, so that the yield is 89.2%. Other reaction conditions were the same as in example 1.
Feed proportioning Example 1 Example 2 Example 3
N-butyraldehyde 100g 100g 100g
Framework nickel 4.5g 4.5g 3g
Skeleton copper 0g 0g 1.5g
Dimethylamine 0g 40g 0g
Liquid nitrogen 15g 0g 15g
Yield is good 85.3% 81.7% 89.2%

Claims (2)

1. The synthesis method of isooctylamine and derivatives by a one-pot method is characterized by comprising the following steps of:
step 1, adding 100 parts by weight of n-butyraldehyde, 4-6 parts by weight of skeleton nickel or skeleton copper or a mixture thereof into a high-pressure reaction kettle, and stirring the reaction kettle at a constant speed of 500r/h under a nitrogen atmosphere of 0.2MPa, wherein the pH=7.5-8 of the pure water washing liquid is 100 parts by weight; the weight ratio of the framework metal to the n-butyraldehyde is 1: 10-1: 100;
step 2, reacting for 1h at the temperature of less than or equal to 25 ℃ under normal pressure, slowly heating to 35 ℃ for 0.5h, slowly heating to 60 ℃ for 0.5h, slowly heating to 90 ℃ for 0.5h, and rapidly cooling to below 35 ℃ in a cooling water environment;
step 3, replacing three times by using 0.2MPa hydrogen, and introducing liquid ammonia or dimethylamine, wherein the feeding mole ratio of the liquid ammonia or dimethylamine to n-butyraldehyde is more than or equal to 0.55:1, charging hydrogen, raising the pressure to 3.0MPa, maintaining the pressure, raising the stirring speed to 700r/h, raising the temperature to 90 ℃ for activating reaction, and after no more hydrogen is absorbed, continuously maintaining for 0.5h, and ending;
and 4, filtering the mother liquor, recovering the catalyst, evaporating ammonia gas at normal pressure, and rectifying and collecting the fraction at 155-156 ℃.
2. The synthesis method according to claim 1, wherein: the weight ratio of the framework metal to the n-butyraldehyde is 1: 20-1: 60.
CN202111581873.2A 2021-12-23 2021-12-23 Synthesis method of isooctylamine and derivative by one-pot method Active CN114105780B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202111581873.2A CN114105780B (en) 2021-12-23 2021-12-23 Synthesis method of isooctylamine and derivative by one-pot method

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202111581873.2A CN114105780B (en) 2021-12-23 2021-12-23 Synthesis method of isooctylamine and derivative by one-pot method

Publications (2)

Publication Number Publication Date
CN114105780A CN114105780A (en) 2022-03-01
CN114105780B true CN114105780B (en) 2024-02-02

Family

ID=80362052

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202111581873.2A Active CN114105780B (en) 2021-12-23 2021-12-23 Synthesis method of isooctylamine and derivative by one-pot method

Country Status (1)

Country Link
CN (1) CN114105780B (en)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB728702A (en) * 1951-12-31 1955-04-27 Ruhrchemie Ag Process for the production of amines
CN1554640A (en) * 2003-12-24 2004-12-15 建德市新化化工有限责任公司 Process for synthesizing iso octyl amine
CN1962604A (en) * 2006-11-29 2007-05-16 建德市新化化工有限责任公司 Method for synthesis of orthooctylamine
CN1984873A (en) * 2004-05-13 2007-06-20 巴斯福股份公司 Method for the continuous production of an amine
CN101880221A (en) * 2010-06-22 2010-11-10 上海师范大学 Process for preparing octenal by one-pot method
CN108603038A (en) * 2016-02-02 2018-09-28 Ａｇｃ株式会社 Near infrared absorbing coloring matter, optical filter and photographic device

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB728702A (en) * 1951-12-31 1955-04-27 Ruhrchemie Ag Process for the production of amines
CN1554640A (en) * 2003-12-24 2004-12-15 建德市新化化工有限责任公司 Process for synthesizing iso octyl amine
CN1984873A (en) * 2004-05-13 2007-06-20 巴斯福股份公司 Method for the continuous production of an amine
CN1962604A (en) * 2006-11-29 2007-05-16 建德市新化化工有限责任公司 Method for synthesis of orthooctylamine
CN101880221A (en) * 2010-06-22 2010-11-10 上海师范大学 Process for preparing octenal by one-pot method
CN108603038A (en) * 2016-02-02 2018-09-28 Ａｇｃ株式会社 Near infrared absorbing coloring matter, optical filter and photographic device

Also Published As

Publication number Publication date
CN114105780A (en) 2022-03-01

Similar Documents

Publication Publication Date Title
CN100591417C (en) Silicon dioxide supported nano-silver catalyst, preparation and use thereof
CN101522600A (en) Process for preparing 1,2-propanediol by hydrogenolysis of glycerol
CN100594210C (en) Process for synthesizing p-aminophenol by nitrobenzene catalytic hydrogenation
CN101362710B (en) Method for preparing aminobenzenesulfonic acid by catalytic hydrogenation
CN102233272A (en) Catalyst for preparing ethylene diamine through amination of ethylene glycol and preparation method thereof
CN109985628A (en) Hydrotalcite composite transition metal catalyst faces the purposes in hydrogen ammonolysis reaction for aldehydes or ketone compounds
CN102432565B (en) Method for preparing 2-hydroxyethylpiperazine
CN102285891A (en) Method for preparing arylamine by catalytic hydrogenation of aromatic nitro compound
CN114105780B (en) Synthesis method of isooctylamine and derivative by one-pot method
CN104387340A (en) Method for preparing N-methyl piperazine and catalyst of N-methyl piperazine
CN102050746A (en) Method for preparing o-chloroaniline
CN101481314B (en) Method for preparing X substituted aniline from X substituted nitrobenzene
CN101434547B (en) Method for preparing aniline from nitrobenzene
CN102351714A (en) Method for preparing p-chloroaniline through catalytic hydrogenation of p-chloronitrobenzene
CN102070693A (en) Method for preparing ursodesoxycholic acid by chiral catalytic hydrogenation of 7-ketodesoxycholic acid
CN101898135B (en) Amorphous catalyst for catalytic hydrogenation of 2-cyan-4-nitroaniline and preparation method of 2,5-diamincyanophenyl
CN101434548B (en) Method for preparing diaminobenzene from dinitro benzene
CN101434550A (en) Method for preparing 1-naphthylamine from 1-nitronaphthalene
CN101514162B (en) Method for preparing X-substituted diaminobenzene from X-substituted dinitrobenzene
CN102351726B (en) Method for synthesizing hydrochloric acid baclofen
CN101798272A (en) Method for synthesizing para aminophenylmethylether by catalytic hydrogenation of paranitroanisole
CN103992230A (en) Method for preparing diaminobenzene and aniline from nitrobenzene mixture containing dinitrobenzene
CN109369408A (en) A method of preparing 2- aminopropanol
CN113713817B (en) Method for preparing n-propanol by catalyzing propanal hydrogenation by nickel-based catalyst
CN109516924B (en) Method for preparing m-aminophenol by catalyzing resorcinol

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant