2549-93-1

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Safety Profile

Moderately toxic by ingestion andskin contact. A severe skin irritant. When heated todecomposition it emits toxic fumes of NOx.

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

Synthetic route

cyclohexane-1,4-dicarbonitrile (10534-13-1) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

Conditions	Yield
With ammonium hydroxide; hydrogen In methanol at 80℃; under 33753.4 Torr; for 4h;	97%
With ammonium hydroxide; hydrogen In methanol at 80℃; under 33753.4 Torr;	97%
With hydrogen In ethanol at 95℃; under 37503.8 Torr; for 0.5h; Temperature;	90%
With hydrogen In ethanol at 95℃; under 37503.8 Torr; for 0.5h;
With hydrogen In ethanol at 95℃; under 37503.8 Torr; for 0.5h;

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;

terephthalonitrile (623-26-7) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

Conditions	Yield
With ammonia; Hexadecane In 1,4-dioxane
In diethylamine
Hydrogenation;

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;

cyclohexylmethyl alcohol (100-49-2) → 4-(aminomethyl)-cyclohexanemethanol (1074-62-0) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 3-azabicyclo[3,2,2]nonane (283-24-9)

Conditions	Yield
With ammonia; hydrogen; Cu#Ni#Cr at 180 - 210℃; under 130050 Torr; Product distribution / selectivity;

bis-1,4-(hydroxymethyl)cyclohexane (105-08-8) → 4-(aminomethyl)-cyclohexanemethanol (1074-62-0) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

Conditions	Yield
With ammonia; chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II) In tetrahydrofuran at 155℃; under 34128.4 Torr; for 12h; Autoclave; Inert atmosphere;

N,N'-cyclohexane-1,4-diyldimethyl-bis-phthalimide (37830-06-1) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

Conditions	Yield
With hydrazine hydrate In ethanol for 4h; Reflux;

cyclohexane-1,4-dicarboxylic acid (619-81-8, 619-82-9, 1076-97-7) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: ammonia; ammonium bicarbonate / water / 190 - 230 °C 2: 245 - 300 °C / 760.05 Torr 3: hydrogen / ethanol / 0.5 h / 95 °C / 37503.8 Torr View Scheme
Multi-step reaction with 3 steps 1: ammonia / 0.5 h / 180 °C 2: phosphorus pentoxide / 1 h / 300 °C 3: hydrogen / ethanol / 0.5 h / 95 °C / 37503.8 Torr View Scheme
Multi-step reaction with 3 steps 1: ammonia / 0.5 h / Heating 2: phosphorus pentoxide / 1 h / 300 °C / 15 - 37.5 Torr / Autoclave 3: hydrogen / ethanol / 0.5 h / 95 °C / 37503.8 Torr View Scheme

bis-1,4-(hydroxymethyl)cyclohexane (105-08-8) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

Conditions	Yield
With chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II); ammonia In tetrahydrofuran at 155℃; under 34128.4 Torr; for 12h;

bis-1,4-(hydroxymethyl)cyclohexane (105-08-8) → 4-(aminomethyl)-cyclohexanemethanol (1074-62-0) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 3-azabicyclo[3,2,2]nonane (283-24-9)

Conditions	Yield
With ammonia; hydrogen In water at 190℃; under 150015 Torr; Overall yield = 87.4 %;
With ammonia; hydrogen In water at 190℃; under 150015 Torr; Temperature; Concentration; Overall yield = 67.0 %;

transcyclohexane-1,4-dicarboxylic acid amide (20101-86-4) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 245 - 300 °C / 760.05 Torr 2: hydrogen / ethanol / 0.5 h / 95 °C / 37503.8 Torr View Scheme
Multi-step reaction with 2 steps 1: phosphorus pentoxide / 1 h / 300 °C 2: hydrogen / ethanol / 0.5 h / 95 °C / 37503.8 Torr View Scheme
Multi-step reaction with 2 steps 1: phosphorus pentoxide / 1 h / 300 °C / 15 - 37.5 Torr / Autoclave 2: hydrogen / ethanol / 0.5 h / 95 °C / 37503.8 Torr View Scheme

tert-butyldicarbonate (34619-03-9) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → [4-(tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester (736054-16-3)

Conditions	Yield
In dichloromethane at 20℃; for 16h;	99%

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + benzaldehyde (100-52-7) → 1,4-bis(benzylideneaminomethyl)cyclohexane (15332-44-2)

Conditions	Yield
at 60℃; under 40 - 60 Torr; for 0.5h;	98%
In ethanol Ambient temperature;

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 4-nitrobenzaldehdye (555-16-8) → C22H24N4O4

Conditions	Yield
In ethanol at 60℃;	98%

cyclohexane-1,4-dicarbonitrile (10534-13-1)

Conditions	Yield
With ammonium hydroxide; hydrogen In methanol at 80℃; under 33753.4 Torr; for 4h;	97%
With ammonium hydroxide; hydrogen In methanol at 80℃; under 33753.4 Torr;	97%
With hydrogen In ethanol at 95℃; under 37503.8 Torr; for 0.5h; Temperature;	90%
With hydrogen In ethanol at 95℃; under 37503.8 Torr; for 0.5h;
With hydrogen In ethanol at 95℃; under 37503.8 Torr; for 0.5h;

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 3-Fluorobenzaldehyde

Conditions	Yield
In ethanol at 60℃;	96%

+ 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N4-{[4-(aminomethyl)cyclohexyl]methyl}-N2-(2-bromobenzyl)-5-nitropyrimidine-2,4-diamine

Conditions	Yield
In dichloromethane at 20℃; for 16h;	89%
In dichloromethane at 20℃; for 16h;	89%

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 4-(2'-benzothienyl)-2-chloropyrimidine (124959-26-8) → [4(cis)-Aminomethylcyclohexylmethyl]-(4-benzo[b]thiophen-2-ylpyrimidin-2-yl)-amine

Conditions	Yield
In isopropyl alcohol at 20 - 110℃; for 20h;	88%

3-chloropyridazine (1120-95-2) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(pyridazin-3-amine) (1454914-58-9)

Conditions	Yield
With 5-chloro-1,3-benzenediamine In 1-methyl-pyrrolidin-2-one at 120℃;	85%

6-chloro-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purine (686344-50-3) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N-{[4-(aminomethyl)cyclohexyl]methyl}-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-amine (1450979-82-4)

Conditions	Yield
In 1,4-dioxane at 80℃; for 16h;	76%

N1,N2-bis(tert-butoxycarbonyl)-N1-(methylcyclopropyl)-S-methylisothiourea (1029434-14-7) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N-(cyclopropylmethyl)-N,N'-bis-(tert-butoxycarbonyl)-N''-[4-(aminomethyl)-cyclohexylmethyl]guanidine (1029434-19-2)

Conditions	Yield
In tetrahydrofuran at 50℃; for 3h;	75%

1,4-benzenedicarboxylic acid dimethyl ester (120-61-6) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → C26H30N2O6

Conditions	Yield
With lithium methanolate In methanol; toluene at 120℃; for 10h;	75%

+ salicylaldehyde → C22H26N2O2 (3353-15-9)

Conditions	Yield
With acetic acid In ethanol for 4h; Reflux;	72.8%

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 6-chloro-(1,2,4,5-tetrazine) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(1,2,4,5-tetrazin-3-amine) (1454914-64-7)

Conditions	Yield
With 5-chloro-1,3-benzenediamine at 110℃; for 24h;	70%

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 4-dimethylamino-benzaldehyde (100-10-7) → C26H36N4 (3245-07-6)

Conditions	Yield
In ethanol at 60℃;	66%

Simazine (122-34-9) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → C15H29N7

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane for 72h; Heating / reflux;	65%

(E)-3-(6,7,8-trimethoxy-2-naphthyl)-2-propenoic acid (203722-23-0) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → 1,4-bis[3-(6,7,8-trimethoxy-2-naphthyl)prop-(2E)-enoylaminomethyl]cyclohexane

Conditions	Yield
	60%

4-chloropyrimidine (17180-93-7) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 8h;	60%

1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

Conditions	Yield
In tetrahydrofuran at 50℃; for 3h;	58%

1,4-bis-(aminomethyl)cyclohexane + 5-chloro-(1,2,4-triazine) (1216085-30-1) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(1,2,4-triazin-5-amine) (1454914-62-5)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 4h; Reflux;	57%

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + Ethyl oxalyl chloride (4755-77-5) → 2,2'-((cyclohexane-1,4-diylbis(methylene))bis(azanediyl))bis(2-oxoacetic acid)

Conditions	Yield
Stage #1: 1,4-bis-(aminomethyl)cyclohexane; Ethyl oxalyl chloride Stage #2: With water; lithium hydroxide In tetrahydrofuran at 20℃; for 12h;	52%

2 chloro-3-methylpyridine (18368-76-8) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(3-methylpyridin-2-amine) (1454914-65-8)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl acetamide at 90℃; for 18h;	45%

2-chloropyrazin (14508-49-7) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(pyrazine-2-amine) (1454914-57-8)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 100℃; for 8h;	45%

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-54-2, 862686-58-6, 1143572-00-2) → 1-(N,N'-diBoc)-guanidinomethyl-4-aminomethylcyclohexane (242452-33-1)

Conditions	Yield
In tetrahydrofuran; dichloromethane; ethyl acetate	43%
In tetrahydrofuran at 20℃; for 0.5 - 3h;	42%

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 1-[(tert-butyloxycarbonylamino)-(tert-butyloxycarbonylimino)-methyl]-1H-pyrazole → 1-(N,N'-di-boc)-guanidinomethyl-4-aminomethylcyclohexane (242452-33-1)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5 - 3h; Product distribution / selectivity;	42%

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-54-2, 862686-58-6, 1143572-00-2) + 1-(N,N'-diBoc)-guanidinomethyl-4-aminomethylcyclohexane

Conditions	Yield
In tetrahydrofuran; ethyl acetate	A n/a B 42%

+ 1,4-bis-(aminomethyl)cyclohexane + 2-Fluorobenzaldehyde (446-52-6) → 3,3'-(cyclohexane-1,4-diylbis(methylene))bis(2-(2-fluorophenyl)-2,3-dihydroquinazolin-4(1H)-one)

Conditions	Yield
With acetic acid for 4h; Reflux;	40%

2,5-dimethyl-3-chloropyrazine (95-89-6) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(3,6-dimethylpyrazin-2-amine) (1454914-66-9)

Conditions	Yield
With caesium carbonate; lithium fluoride In N,N-dimethyl-formamide at 135℃; for 16h;	35%

2-fluoropyridine (372-48-5) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(pyridin-2-amine) (1454914-56-7)

Conditions	Yield
at 100 - 150℃; for 10h;	30%

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + (E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid (28010-23-3) → N,N'-bis[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoyl]-1,4-bis(aminomethyl)cyclohexane

Conditions	Yield
	18%

Upstream product

• 623-26-7 terephthalonitrile 
• 100-49-2 cyclohexylmethyl alcohol 
• 105-08-8 bis-1,4-(hydroxymethyl)cyclohexane 
• 619-81-8 cyclohexane-1,4-dicarboxylic acid 
• 10534-13-1 cyclohexane-1,4-dicarbonitrile 
• 20101-86-4 transcyclohexane-1,4-dicarboxylic acid amide 
• 37830-06-1 N,N'-cyclohexane-1,4-diyldimethyl-bis-phthalimide 
• 33424-83-8 1,4-cyclohexanedicarboxaldehyde 
• 55309-54-1 cis/trans-1,3-cyclohexanedicarboxaldehyde 

Downstream Products

• 15332-46-4 1,4-Cyclohexan-N,N,N',N'-tetrakis-(2-hydroxyethyl)-bis-(methylamin) 
• 55778-76-2 N,N'-(1,4-cyclohexylenebismethyl)bis[N-methyl-2-hydroxydecylamine] 
• 55778-73-9 N,N'-(1,4-cyclohexylenebismethyl)-bis[2-hydroxydecylamine] 
• 55778-77-3 N,N'-(1,4-cyclohexylenebismethyl)-bis[2-hydroxydodecylamine] 
• 61796-64-3 N,N'-Bis-(10-undecenoylaminomethyl)-cyclohexan 
• 15332-44-2 1,4-bis(benzylideneaminomethyl)cyclohexane 
• 55778-72-8 N,N'-(1,4-cyclohexylenebismethyl)-bis[2-hydroxyoctylamine] 
• 3245-07-6 C₂₆H₃₆N₄ 
• 3245-00-9 C₂₂H₂₄F₂N₂ 
• 514832-35-0 N₄-(4-aminomethyl-cyclohexylmethyl)-5-nitro-N₂-(2-chloro-benzyl)-pyrmidine-2,4-diamine 

Relevant academic research and scientific papers

METHOD FOR PREPARING DICYANOALKANE AND BIS(AMINOMETHYL)ALKANE

A method for preparing a dicyanoalkane may omit a filtration for a catalyst after a cyanation reaction can by carrying out the cyanation reaction in a state in which precipitation of a metal catalyst is suppressed. A method for preparing a dicyanoalkane may involve cyanating one or more aliphatic dicarboxylic acids and/or salt(s) thereof with an ammonia source in the presence of a predetermined compound and a catalyst, wherein, in the cyanation, the amount of the predetermined compound is maintained at a predetermined amount or more with respect to the catalyst.

METHOD FOR PRODUCING DICYANOCYCLOHEXANE AND BIS(AMINOMETHYL)CYCLOHEXANE

The problem addressed by this invention is to achieve a useful and novel method for producing dicyanocyclohexane and bis(aminomethyl)cyclohexane. This problem was solved by providing a method for producing dicyanocyclohexane having a cyanation step in which dicyanocyclohexane is obtained by a cyanation reaction of cyanocyclohexane-1-carboxylic acid and/or a salt thereof with an ammonia source, and a method for producing bis(aminomethyl)cyclohexane using the dicyanocyclohexane thus produced.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a preparation method of nitrile. Compared with the prior art, the preparation method has the characteristics of obvious reduction of the usage amount of ammonia sources, low environmental pressure, low energy consumption, low production cost, high purity and yields of nitrile products, and the like, and can be used for obtaining nitrile with a more complex structure. The invention also relates to a method for preparing corresponding amine with nitrile.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a preparation method of nitrile. Compared with the prior art, the preparation method has the characteristics of obvious reduction of the usage amount of ammonia sources, low environmental pressure, low energy consumption, low production cost, high purity and yields of nitrile products, and the like, and can be used for obtaining nitrile with a more complex structure. The invention also relates to a method for preparing corresponding amine with nitrile.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a preparation method of nitrile. Compared with the prior art, the preparation method has the characteristics of obvious reduction of the usage amount of ammonia sources, low environmental pressure, low energy consumption, low production cost, high purity and yields of nitrile products, and the like, and can be used for obtaining nitrile with a more complex structure. The invention also relates to a method for preparing corresponding amine with nitrile.

Steric effects in the catalytic amination of γ-, δ-, and ε-glycols

The amination of butane-1,4-diol, isomeric dipropylene glycols, and cyclohexane-1,4-diyldimethanol in the presence of nickel/copper/chromium catalysts has been studied. The effect of the initial glycol structure on the reaction selectivity has been estima

· Uniform catalyst by using alcohol aminosilicone di-, tri-and a method of manufacturing a polyphenylenepolyamine

The invention relates to a method for producing primary amines, which contain at least one functional group of the formula (-CH2-NH2) and at least one further primary amino group, by the alcohol amination of reactants, which contain at least one functional group of the formula (-CH2-OH) and at least one further functional group (-X), wherein (-X) is selected from hydroxyl groups and primary amino groups, using ammonia with removal of water, wherein the reaction is carried out in a homogeneously catalyzed manner in the presence of at least one complex catalyst containing at least one element selected from groups 8, 9 and 10 of the periodic table and at least one donor ligand.

Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca2+-activated K+ channels

Previously, quinolinium-based tetraazacyclophanes, such as UCL 1684 and UCL 1848, have been shown to be extraordinarily sensitive to changes in chemical structure (especially to the size of the cyclophane system) with respect to activity as potent non-peptidic blockers of the small conductance Ca 2+-activated K+ ion channels (SKCa). The present work has sought to optimize the structure of the linking chains in UCL 1848. We report the synthesis and SKCa channel-blocking activity of 29 analogues of UCL 1848 in which the central CH2 of UCL 1848 is replaced by other groups X or Y = O, S, CF2, CO, CHOH, CC, CHCH, CHMe to explore whether subtle changes in bond length or flexibility can improve potency still further. The possibility of improving potency by introducing ring substituents has also been explored by synthesizing and testing 25 analogues of UCL 1684 and UCL 1848 with substituents (NO2, NH2, CF 3, F, Cl, CH3, OCH3, OCF3, OH) in the 5, 6 or 7 positions of the aminoquinolinium rings. As in our earlier work, each compound was assayed for inhibition of the afterhyperpolarization (AHP) in rat sympathetic neurons, an action mediated by the SK3 subtype of the SK Ca channel. One of the new compounds (39, R7 = Cl, UCL 2053) is twice as potent as UCL 1848 and UCL 1684: seven are comparable in activity.

PROCESS FOR PREPARING DI-, TRI- AND POLYAMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION

Process for preparing primary amines which have at least one functional group of the formula (—CH2—NH2) and at least one further primary amino group by alcohol amination of starting materials having at least one functional group of the formula (—CH2—OH) and at least one further functional group (—X), where (—X) is selected from among hydroxyl groups and primary amino groups, by means of ammonia with elimination of water, wherein the reaction is carried out homogeneously catalyzed in the presence of at least one complex catalyst comprising at least one element selected from groups 8, 9 and 10 of the Periodic Table and also at least one donor ligand.

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.