2579-20-6

Usage

Uses

Used in Chemical Synthesis:
1,3-Cyclohexanebis(methylamine) is used as an organic intermediate for the synthesis of various compounds, contributing to the development of new materials and products in the chemical industry.
Used as Epoxy Curing Agents:
In the manufacturing of epoxy resins, 1,3-Cyclohexanebis(methylamine) is used as a curing agent, which helps in hardening and setting the epoxy material, making it suitable for various applications such as coatings, adhesives, and composites.
Used in Fiber-Based Membranes:
1,3-Cyclohexanebis(methylamine) is used as a cross-linking agent in the formation of fiber-based membranes for the separation of CO2. This application is particularly relevant in the field of environmental technology and energy production, where CO2 capture and separation are crucial for reducing greenhouse gas emissions.
Used in Synthesis of Open-Framework Bimetallic Phosphites:
1,3-Cyclohexanebis(methylamine) is also used in the synthesis of open-framework bimetallic phosphites, which have potential applications in molecular sieves and ion exchangers. This contributes to the development of advanced materials for gas separation, catalysis, and other industrial processes.

Safety Profile

Poison by skin contact andintraperitoneal routes. Moderately toxic by ingestion.When heated to decomposition it emits toxic fumes ofNOx.

InChI:InChI=1/C8H18N2/c9-5-7-2-1-3-8(4-7)6-10/h7-8H,1-6,9-10H2/p+2/t7-,8-/m0/s1

Synthetic route

1,3-di(aminomethyl)benzene (1477-55-0) → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

Conditions	Yield
With 5% active carbon-supported ruthenium; lithium nitrate; hydrogen In isopropyl alcohol at 120℃; under 40504.1 Torr; for 0.333333h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	90.6%
With hydrogen; sodium hydroxide In 1,4-dioxane at 70℃; under 37503.8 - 45004.5 Torr; for 0.01h; Temperature;	90%
With hydrogen; ruthenium(IV) oxide In ethanol

C9H14N2O2 → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

Conditions	Yield
With hydrazine hydrate; sodium hydroxide In 1,4-dioxane at 120℃; for 18h; pH=10;	88%

1,4-cyclohexanedicarboxaldehyde (33424-83-8) + cis/trans-1,3-cyclohexanedicarboxaldehyde (55309-54-1) → 3-azabicyclo<3.3.1>nonane (280-70-6) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

Conditions	Yield
Stage #1: 1,4-cyclohexanedicarboxaldehyde; cis/trans-1,3-cyclohexanedicarboxaldehyde With ammonia In methanol at 100℃; for 0.666667 - 0.75h; Stage #2: With hydrogen; Ni catalyst supported on silica/alumina In methanol at 100℃; under 41372.9 Torr; for 5h; Product distribution / selectivity;	A 27% B n/a C n/a
With ammonia; hydrogen; Ni-5256W In methanol at 120℃; under 15514.9 - 51716.2 Torr; for 3h; Product distribution / selectivity;	A 5% B n/a C n/a
With ammonia; hydrogen; Ni-5256W In methanol at 120 - 130℃; under 15514.9 - 51716.2 Torr; for 3 - 5h; Product distribution / selectivity;
Stage #1: 1,4-cyclohexanedicarboxaldehyde; cis/trans-1,3-cyclohexanedicarboxaldehyde With ammonia; Ni catalyst supported on silica/alumina In methanol at 20 - 100℃; for 0.666667 - 0.75h; Stage #2: With hydrogen; Ni catalyst supported on silica/alumina In methanol at 100℃; under 41372.9 Torr; Product distribution / selectivity;

1,3-bis(salicylidiniminomethyl)cyclohexane → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + salicylaldehyde (90-02-8)

Conditions	Yield
With water at 30℃; Rate constant; var. pH;

benzene-1,3-dicarbonitrile (626-17-5) → m-xylylenediamine + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

Conditions	Yield
With hydrogen; 2% ruthenium/alumina In 1,4-dioxane; ammonia at 120℃; under 112511 Torr;

m-xylylenediamine → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

Conditions	Yield
With hydrogen; 5 wt% Ru/C In ammonia at 120℃; under 75007.5 Torr;

1,4-cyclohexanedicarboxaldehyde (33424-83-8) + cis/trans-1,3-cyclohexanedicarboxaldehyde (55309-54-1) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

Conditions	Yield
With ammonia; hydrogen; Ni-5256W In methanol at 130℃; under 15514.9 - 51716.2 Torr; for 5h; Product distribution / selectivity;
With ammonia; hydrogen; Ni-5256P In methanol at 120℃; under 65783 - 68368.8 Torr; for 6.21667h; Product distribution / selectivity;
With ammonia; hydrogen; Raney nickel Ni-5256 In methanol at 130℃; under 15514.9 - 51716.2 Torr; for 15 - 19.5h; Product distribution / selectivity;

benzene-1,3-dicarbonitrile (626-17-5) → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

Conditions	Yield
Hydrogenation;

cyclohexane-1,2-epoxide (286-20-4) → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen / 220 °C / 760.05 Torr 2: tetraethylammonium hydroxide / 1,4-dioxane / 8.75 h / 90 °C 3: hydrogen; nickel(II) chloride hexahydrate / 8 h / 70 °C / 30003 Torr View Scheme

1,3-dicyano-1-cyclohexanol (100377-18-2) → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

Conditions	Yield
With nickel(II) chloride hexahydrate; hydrogen at 70℃; under 30003 Torr; for 8h; Reagent/catalyst; Temperature; Pressure;

3,4-dimethylbenzaldehyde (5973-71-7) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → C26H34N2 (1217526-73-2)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

m-bromobenzoic aldehyde (3132-99-8) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → C22H24Br2N2 (1217527-02-0)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

4-tert-Butylbenzaldehyde (939-97-9) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → C30H42N2 (1217526-91-4)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2,5-dimethylbenzaldehyde (5779-94-2) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → C26H34N2 (1217526-78-7)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

3,5-dimethylbenzaldehyde (5779-95-3) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → C26H34N2 (1217526-72-1)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-n-propylbenzaldehyde (28785-06-0) → C28H38N2 (1217526-85-6)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-(n-butyl)benzaldehyde (1200-14-2) → C30H42N2 (1217526-89-0)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-methyl-benzaldehyde (104-87-0) → C24H30N2 (1217526-68-5)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-fluorobenzaldehyde (459-57-4) → C22H24F2N2 (1217527-04-2)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-chlorobenzaldehyde (104-88-1) → C22H24Cl2N2 (1217526-94-7)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 2,6-dichlorobenzaldehyde (83-38-5) → C22H22Cl4N2 (1217526-98-1)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 3-nitro-benzaldehyde (99-61-6) → C22H24N4O4 (1217527-06-4)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + benzaldehyde (100-52-7) → C22H26N2 (2539-69-7)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 3-Chlorobenzaldehyde (587-04-2) → C22H24Cl2N2 (1217526-97-0)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-bromo-benzaldehyde (1122-91-4) → C22H24Br2N2 (1217527-00-8)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 2,4-dimethylbenzaldehyde (15764-16-6) → C26H34N2 (1217526-81-2)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 2-methylphenyl aldehyde (529-20-4) → C24H30N2 (1217526-75-4)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-ethylbenzylaldehyde (4748-78-1) → C26H34N2 (1217526-83-4)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + (4-isopropylbenzaldehyde) (122-03-2) → C28H38N2 (1217526-87-8)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + m-tolyl aldehyde (620-23-5) → C24H30N2 (1217526-70-9)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 3-Fluorobenzaldehyde (456-48-4) → C22H24F2N2 (1217527-05-3)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + carbonic acid dimethyl ester (616-38-6) → 1,3-bis(methoxycarbonylaminomethyl)cyclohexane

Conditions	Yield
lipase from Candida antarctica In toluene at 70℃; for 48h; Product distribution / selectivity;	99%
With sodium methylate In methanol; water at 50℃; for 7h;	97%
With water; sodium methylate In methanol; acetone at 50℃; for 5.5h; Solvent;	95.5%

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + epichlorohydrin (106-89-8) → N,N,N',N'tetraglycidyl-1,3-bis-(aminomethyl) cyclohexane (65992-66-7)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; toluene at 90℃; for 1h; Product distribution / selectivity; Inert atmosphere;	97.2%

phosgene (75-44-5) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2)

Conditions	Yield
Stage #1: cis, trans-1,3-dimethylaminocyclohexane With hydrogenchloride In chlorobenzene at 30 - 45℃; for 3.5h; Large scale; Stage #2: phosgene In chlorobenzene at 60℃; Large scale;	96.5%
Stage #1: cis, trans-1,3-dimethylaminocyclohexane With carbon dioxide In toluene at 25 - 30℃; for 1.33333h; Stage #2: phosgene In toluene at 25 - 90℃; for 23h;
Stage #1: cis, trans-1,3-dimethylaminocyclohexane With hydrogenchloride In water; toluene at 20℃; for 0.5h; Stage #2: phosgene With N,N-dimethyl-formamide In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 5h; Solvent;
In 1,2-dichloro-benzene at 0 - 130℃; for 11h; Solvent; Temperature;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + Diethyl carbonate (105-58-8) → 1,3-bis(ethoxycarbonylaminomethyl)cyclohexane

Conditions	Yield
With sodium methylate In methanol at 50℃; for 6h;	95.9%
With water; sodium methylate In methanol at 50℃; for 6.5h;	95.9%

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → α,α'-bis(2-hydroxy-1-naphthaliminomethyl)-1,3-cyclohexane

Conditions	Yield
In methanol for 4h; Reflux;	95%

cycl-isopropylidene malonate (2033-24-1) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + trimethyl orthoformate (149-73-5) → C22H30N2O8

Conditions	Yield
Stage #1: cycl-isopropylidene malonate; trimethyl orthoformate for 1h; Reflux; Stage #2: cis, trans-1,3-dimethylaminocyclohexane for 2h; Reflux;	92%

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + salicylaldehyde (90-02-8) → α,α'-bis(salicyliminomethyl)-1,3-cyclohexane (183246-63-1)

Conditions	Yield
In methanol for 4h; Reflux;	91%

phthalic anhydride (85-44-9) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → N,N'-cyclohexane-1,3-diyldimethyl-bis-phthalimide (942291-68-1)

Conditions	Yield
With acetic acid Heating;	90%

Upstream product

• 1477-55-0 1,3-di(aminomethyl)benzene 
• 626-17-5 benzene-1,3-dicarbonitrile 
• 33424-83-8 1,4-cyclohexanedicarboxaldehyde 
• 55309-54-1 cis/trans-1,3-cyclohexanedicarboxaldehyde 
• 100377-18-2 1,3-dicyano-1-cyclohexanol 
• 286-20-4 cyclohexane-1,2-epoxide 

Downstream Products

• 108559-85-9 1-N-(4'-hydroxy)butanoylaminomethyl-3-aminomethylcyclohexane 
• 4425-82-5 9-methylene-fluorene 
• 106-47-8 4-chloro-aniline 
• 942291-68-1 N,N'-cyclohexane-1,3-diyldimethyl-bis-phthalimide 
• 242452-34-2 1-(N,N'-di-boc)-guanidinomethyl-3-aminomethylcyclohexane 
• 743460-78-8 5-[(R)-2-[(3-Aminomethylcyclohexylmethyl)amino]-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one 
• 242452-34-2 1-(N,N'-diBoc)-guanidinomethyl-3-aminomethylcyclohexane 

Relevant academic research and scientific papers

Preparation process of 1, 3-cyclohexanediamine

The invention discloses a preparation process of 1, 3-cyclohexane dimethylamine, and the process comprises the following steps: 1) isomerization dehydrogenation of cyclohexene oxide: converting cyclohexene oxide into cyclohexenone under the action of an isomerization dehydrogenation catalyst; 2) addition of cyclohexenone and hydrocyanic acid: reacting cyclohexenone under the action of hydrocyanicacid and an alkaline addition catalyst to generate 1, 3-dicyano-1-cyclohexanol; 3) dehydration and hydrogenation of 1, 3-dicyano-1-cyclohexanol: carrying out dehydration and hydrogenation on the obtained 1, 3-dicyano-1-cyclohexanol in the presence of hydrogen and a hydrogenation catalyst to generate 1, 3-cyclohexanediamine. Compared with the prior art, the invention has the beneficial effects thatthe raw materials are cheap and easy to obtain; the reaction yield is high, and the total yield is greater than or equal to 90%; the reaction conditions are mild and suitable for industrialization.

Preparation method of 1, 3-cyclohexanebis(methylamine)

The invention provides a preparation method of 1, 3-cyclohexanebis(methylamine), specifically comprising the following steps: 1, carrying out double Mannich reaction on cyclohexanone, formaldehyde andurea under acidic conditions to obtain an intermediate; and 2, letting the intermediate prepared in the previous step react with hydrazine hydrate under the alkaline condition, wherein on one hand, ketone carbonyl is reduced into methylene (Wolf-Kishner reduction) through hydrazine hydrate, and meanwhile, hydrazinolysis is conducted on acylamino through hydrazine hydrate, two amido groups are exposed, and finally 1, 3- cyclohexanebis(methylamine) is prepared. According to the method, under the condition that high-pressure hydrogenation is not used, cyclohexanone, formaldehyde and urea can beefficiently converted into 1, 3-cyclohexanebis(methylamine). The method is simple to operate; and the reagent is cheap and easily available, green and safe, efficient and environmentally-friendly, andsuitable for industrial production.

Ru/g-C3N4as an efficient catalyst for selective hydrogenation of aromatic diamines to alicyclic diamines

A series of Ru/g-C3N4materials with highly dispersed Ru were firstly prepared by an ultrasonic impregnation method using carbon nitride as a support. The catalysts were characterized by various techniques including BET and elemental analysis, ICP-AES, XPS, XRD, CO2-TPD and TEM. The results demonstrated that Ru/g-C3N4materials with a mesoporous structure and highly dispersed Ru were successfully prepared. The chemo-selective hydrogenation ofp-phenylenediamine (PPDA) to 1,4-cyclohexanediamine (CHDA) over Ru/g-C3N4as a model reaction was investigated in detail. PPDA conversion of 100% with a CHDA selectivity of more than 86% could be achieved under mild conditions. It can be inferred that the carbon nitride support possessed abundant basic sites and the Ru/g-C3N4-Tcatalysts provided suitable basicity for the aromatic ring hydrogenation. Compared to the N-free Ru/C catalyst, the involvement of nitrogen species in Ru/g-C3N4remarkably improved the catalytic performance. In addition, the recyclability of the catalyst demonstrated that the aggregation of Ru nanoparticles was responsible for the decrease of the catalytic activity. Furthermore, this strategy also could be expanded to the selective hydrogenation of other aromatic diamines to alicyclic diamines.

A continuous hydrogenation reduction aromatic amine preparation [...] device and method

The present invention relates to the technical field of catalytic hydrogenation, in particular to a continuous hydrogenation reduction aromatic amine preparation [...] device and method. The device comprises a raw material tank (9), the cylinder (8), the micro-mixer (1), micro-packed bed (2), delay pipeline (3) and gas-liquid separation tank (4). Continuous hydrogenation reduction aromatic amine preparation [...] method of containing aromatic amine of reaction liquid and hydrogen at the same time continuous access micro-mixer (1) in the gas-liquid two phase uniformly and fully mixed, continuous contact with the catalyst after mixing to carry out gas-liquid-solid three-phase hydrogenation reduction reaction, the reaction liquid phase after the product obtained after the rectification [...] product. The present invention realizes big flow of the continuous production of the alicyclic amine compound, and has realized the micro-reaction system combined with the packed bed, and micro-reaction system [...] stock of the furnace body is small, thereby improving the controllability of the catalytic hydrogenation reaction and safety.

A process for preparing 1, 3 - cyclohexyl dimethylamine method

The invention relates to a process for preparing 1, 3 - cyclohexyl dimethylamine method, in the same solvent under a two-stage hydrogenation, 1st stage hydrogenation to Raney nickel as catalyst, methanol, methylamine or 1, 4 - dioxane in one or several kinds of solvent, organic amine, liquid ammonia, water or sodium hydroxide as adjuvant, the reaction temperature is 40 - 80 °C, the reaction pressure is 5 - 8 mpa lower, isophthalonitrile and hydrogen to carry out the reaction, the reaction time is 1 - 5 h, xylylene amine reaction solution obtained, 2nd section carries the ruthenium hydrogenation by load of the active carbon as catalyst, when the reaction temperature is 80 - 130 °C, reaction pressure is 5 - 8 mpa lower, a xylylene amine reaction liquid and hydrogen to continue to carry out the reaction, the reaction time is 1 - 6 h, preparation of the 1, 3 - cyclohexyl dimethylamine. The total yield of the present invention can be up to 90%. The technological process is simple, high yield, easy to rectification, can be directly in the prior MXDA production process is improved on, easy industrialization.

Method for preparing 1,3-cyclohexanedimethanamine

The invention relates to a method for preparing 1,3-cyclohexanedimethanamine. The method comprises the following steps: two stages of hydrogenation are performed under a same solvent, wherein first-stage hydrogenation uses Raney nickel as a catalyst, one or more of the group consisting of methanol, methylamine and 1,4-dioxane is taken as a solvent, an organic amine, liquid ammonia, water or sodiumhydroxide is taken as an auxiliary agent, and under the reaction temperature of 40-80 DEG C and the reaction pressure of 5-8MPa, isophthalonitrile reacts with a hydrogen gas for 1-5h to obtain a m-xylylenediamine reaction liquid; and second-stage hydrogenation uses ruthenium supported activated carbon as a catalyst, and under the reaction temperature of 80-130 DEG C and the reaction pressure of 5-8MPa, the m-xylylenediamine reaction liquid reacts with a hydrogen gas for 1-6h to prepare the 1,3-cyclohexanedimethanamine. According to the method provided by the invention, the total yield can reach 90%; and the process has simple operation and a high yield, rectification is easy, and the process can be directly modified based on a current MXDA production process, thereby facilitating industrialization.

Effect of alkali metal nitrates on the ru/c-catalyzed ring hydrogenation of m-xylylenediamine to 1,3-cyclohexanebis(methylamine)

Ru/C-catalyzed hydrogenation of m-xylylene diamine into 1,3-cyclohexanebis(methylamine) was greatly accelerated by the presence of LiNO3, NaNO2, or NaNO3. It was found that the effect of the nitrate salt was significantly affected by the size of cation. The promoting effect of the nitrate salt increased with the decrease of the cation size: LiNO3 ~ NaNO3 > KNO3 > CsNO3 [1-butyl-3-methylimidazolium]NO3. XRD analysis of the recovered catalysts after the hydrogenation reactions showed that LiNO3 and NaNO3 were completely transformed into LiOH and NaOH, respectively, along with the evolution of NH3, while KNO3 and CsNO3 remained unchanged.

METHOD OF CONVEYING LIQUIDS

The present invention relates to a method of continuously conveying a liquid which is used as starting material in a chemical reaction by means of a displacement pump having physically separate forward-transport valves and a liquid-filled bidirectional flow line between displacement pump and forward-transport valves, wherein an auxiliary liquid which is a product or a starting material of the chemical reaction and has a melting point which is below the melting point or below the saturation temperature of the liquid to be conveyed is present in the bidirectional flow line. The present invention additionally provides for the use of a product formed by hydrogenation of an aromatic compound as auxiliary liquid for conveying an aromatic compound and also the use of an alcohol or an ester derived from alcohol and carboxylic acid as auxiliary liquid for conveying carboxylic acids or carboxylic acid derivatives.

PROCESS FOR THE REDUCTIVE AMINATION OF ALDEHYDES AND KETONES

Aldehyde or ketone compounds having more than one carbonyl group are reductively aminated to form a product amine compound having more than one primary amino group. The aldehyde or ketone compound is reacted with the product amine compound in the presence of an alcohol solvent, to form a reaction mixture that contains one or more intermediates. The intermediate is then reductively aminated to form the desired product. This process may produce the desired product in very high yields with low levels of secondary amine impurities.

PROCESS FOR THE REDUCTIVE AMINATION OF ALDEHYDES AND KETONES VIA THE FORMATION OF MACROCYCLIC POLYIMINE INTERMEDIATES

Aldehyde or ketone compounds having more than one carbonyl group are reductively aminated to form a product amine compound having more than one primary amino group. The aldehyde or ketone compound is reacted with the product amine compound, to form a reaction mixture that contains one or more intermediates. The intermediate is then reductively aminated to form the desired product. This process produces the desired product in very high yields with low levels of secondary amine impurities.