CN105418364A - Process and plant for producing fatty alcohols - Google Patents
Process and plant for producing fatty alcohols Download PDFInfo
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- CN105418364A CN105418364A CN201510582697.2A CN201510582697A CN105418364A CN 105418364 A CN105418364 A CN 105418364A CN 201510582697 A CN201510582697 A CN 201510582697A CN 105418364 A CN105418364 A CN 105418364A
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- fatty acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
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Abstract
The present invention relates to a process and a plant for producing fatty alcohols from a reaction mixture containing at least one fatty acid ester and at least one free fatty acid, wherein the at least one fatty acid ester is hydrogenated with hydrogen to at least one fatty alcohol, wherein the hydrogenation is effected on a catalyst at a temperature of 150 to 300 DEG C and a pressure of 50 to 250 bar, and wherein the content of the at least one free fatty acid in the reaction mixture is lowered before the hydrogenation.
Description
Technical field
The present invention relates to the method and apparatus for producing fatty alcohol from the reaction mixture containing at least one fatty acid ester and at least one free fatty acids, be wherein at least one fatty alcohol with hydrogen by the hydrogenation of described at least one fatty acid ester, wherein under the pressure of the temperature of 150 to 300 DEG C and 50 to 250 bar, carry out described hydrogenation on a catalyst.
Background technology
Fatty alcohol mainly has the straight chain simple function terminal alcohol that chain length is the alkyl group of 8 to 18 C atoms.In general, fatty alcohol is hydrogenation by lipid acid or the corresponding esters of fatty acid mixt, particularly methyl esters and obtains from renewable raw materials.Such as at " Liv Ullmann industrial chemistry encyclopaedia (Ullmanns
derTechnischenChemie) ", the third edition, the 7th volume, describes this production method of fatty alcohol in the 440th page and the page number afterwards.This catalyzed reaction is carried out according to following reaction scheme:
R
1=C
nh
2n+1, and n=7 ~ 17
R
2=C
nh
2n+1, and n=1 ~ 18
Due to the esterification of its production, free fatty acids, as the free fatty acids of fatty acid ester still containing residual volume of raw material.The content of free fatty acids can be determined by the consumption of alkaline titrant potassium hydroxide (KOH) by titration mode.It provides so-called in the acid number (fatty acid ester) of unit mg (KOH)/g based on fatty acid ester amount used by the consumption of mg.The technical purity of fatty acid ester is in the acid value of 0.5 to 1.0mg (KOH)/g (fatty acid ester).
US6187974 describes a kind of method of producing fatty alcohol from oreodaphene.Oreodaphene is vegetables oil Oleum Cocois and palm-kernel oil, is because they have the lauric acid of high-content.The lauric acid derived from alkane n-dodecane is by depickling and the step of transesterification of base catalysis, be corresponding fatty acid methyl ester and purifying by methanol conversion subsequently.Selective hydration is carried out to the fatty acid methyl ester of purifying, to obtain corresponding fatty alcohol.
The something in common of this and similar method for hydrogenation is, catalyzer shows the catalyst activity of reduction in the process of described method.
The activity of this reduction causes the following fact: must obviously extend the fatty acid ester residence time in the reactor to realize high transformation efficiency, or no longer realize transforming completely at all.Particularly in operation at industrial scale, there is following problem: constantly more catalyst changeout, this relates in one aspect to the high cost about raw catalyst or catalyst regeneration, and causes the lengthy shut down of equipment on the other hand.
Summary of the invention
Therefore, the object of this invention is to provide the method making the hydrogenation catalyst of fatty acid ester stably keep activity within the time extended.
This purpose is achieved by the method with the application.In the process, be corresponding fatty alcohol by the reaction mixture hydrogenation containing at least one fatty acid ester and at least one non-esterified free fatty acid on a catalyst.Described hydrogenation is carried out at the temperature of 150 to 300 DEG C and 50 to 300 pressure clung to.According to the present invention, before hydrogenation, reduce the amount of free fatty acids contained in reaction mixture, the productive rate of the more long life of catalyzer and the raising about fatty alcohol can be realized thus.
The present invention is based on following discovery: free fatty acids contained in mixture is converted into corresponding alcohol equally according to following reaction in principle
Wherein R=C
nh
2n+1, and n=7 ~ 17,
But as long as they are included in system, they just occupy and block the free active centre of used catalyst.
Particularly when carrying out hydrogenation at the temperature at 170 to 220 DEG C and/or under the pressure of 50 to 100 bar, this effect is conclusive for gained conversion value, because under these conditions, the conversion of free fatty acids be carry out under the speed obviously slowed down and therefore described free fatty acids corresponding long-time in be present in system.
The following impact that can prevent previous observation from arriving by the amount reducing free fatty acids contained in reaction mixture: in the hydrogenation experiment within the scope of middle pressure, the catalytic activity of the catalyzer in heterogeneous introducing reaction mixture obviously reduces the incidence leached with so-called catalyzer and increases, and namely occurs the release in active centre.Therefore, also can when not increasing catalyst consumption amount and use about the similar process costs that carries out operating to carry out being pressed in fatty alcohol.This has economic interests especially, and reason is, due to and the environment division of not all must designed to be used high pressure range, and make the cost of investment of this equipment be starkly lower than high-tension apparatus.Calculate and disclose, be the medium size installations of 100kt/a for throughput, cost of investment saves about 15-20%.
Particularly when catalyzer exists in solid form, need to remove free fatty acids contained in reaction mixture at least partly, this is because when solid catalyst system, these lipid acid occupy catalytic surface temporarily and therefore occur that catalyst activity reduces in for a long time.
Preferably, catalyzer used is metal catalyst, is particularly preferably copper-based catalysts, is preferably based on copper chromite.Copper containing catalyst tool has the following advantages: fatty acid ester is converted into fatty alcohol with very large selectivity by it under high space/time productive rate.The catalyzer based on copper and copper chromite with the difference doping of iron or manganese is particularly preferred.When using metal catalyst, particularly when using copper containing catalyst, disclose the corrosion property of free fatty acids especially consumingly.Find in laboratory experiment, the degraded of metallic surface is carried out so strong, to such an extent as to when using copper containing catalyst, this degraded even becomes visually visible in the reaction product with copper-micro-red stain look form.Therefore, particularly when use metal catalyst time, must before carrying out actual hydrogenation in mode according to the present invention at least in part remove or in and free fatty acids, to reach acceptable conversion value.
In addition, found that acid number free fatty acids amount contained in reaction mixture being reduced to≤0.1mg (KOH)/g (fatty acid ester) is particularly advantageous.Therefore acid number is so low to such an extent as to almost can gets rid of occupying of described impact, i.e. active catalytic center completely.
The reduction of free fatty acids amount contained in realization response mixture can be carried out by adding alkali.By forming corresponding salt, described free fatty acids can its fatty acid salt remove and the amount of the acidic-group existed in reaction mixture can obviously reduce.
As alkali, preferably using NaOH or KOH, is that it has so high basicity to such an extent as to neutralization reaction completely almost occurs because these alkali are the materials that can obtain with low cost.
Then be the separation of soap after this neutralization, the water washing preferably carried out in post, and drying.
In addition, can by the amount using ion-exchanger to reduce free fatty acids contained in reaction mixture.This tool has the following advantages: the number destroying the acidic-group of catalyzer reduces, and does not have salt formation in the reactive mixture.In principle, use is in its OH
-the basic anion interchanger of form, Here it is for where only the corresponds to fatty acid concentration water yield between commutation period is released into the reason of pending fatty acid ester.Lipid acid is retained in ion-exchanger.
A favourable aspect of the present invention provides and uses fatty acid methyl ester as fatty acid ester, is because can easily separating obtained short chain alcohol methyl alcohol.At industrial scale, be almost produce fatty acid methyl ester by the transesterification reaction of tri-glyceride and methyl alcohol completely.Except fatty acid methyl ester, identical degree is also the fatty acid ester (so-called wax ester) of fatty alcohol for the raw material of method for hydrogenation according to the present invention.But in principle, other fatty acid ester, particularly short chain alcohol, as the ester of ethanol or propyl alcohol, are also possible.
When using fatty acid methyl ester, except corresponding fatty alcohol, during its hydrogenation, also obtain methyl alcohol.When reaction product (fatty alcohol) is brought down below the value of the dividing potential drop at indivedual temperature that methyl alcohol exists in the reactor at the pressure of reactor exit, the residual volume staying the methyl alcohol in product stream can evaporate and can obtain hardly containing the product of methyl alcohol.
The present invention comprises a kind of equipment in addition, and it according to described method, produces fatty alcohol from the reaction mixture containing at least one fatty acid ester and at least one free fatty acids for preferably.This equipment is provided for the reactor of hydrogenated fat acid esters on a catalyst under the pressure of the temperature of 150 to 250 DEG C and 50 to 300 bar.Described reactor also comprises the gas introducing apparatus for introducing hydrogen.According to the present invention, described equipment comprises the instrument for reducing free fatty acids amount contained in the reactive mixture before hydrogenation.Utilize this equipment to arrange, reliably can prevent the catalytic activity strongly reducing catalyzer due to the free fatty acids of existence.
Of the present invention one preferred in, reactor be designed to 170 to 220 DEG C temperature and 50 to 100 bar pressure under hydrogenation.This design tool has the following advantages: the cost of investment for the production of the equipment of fatty alcohol is starkly lower than the known device of the high pressure range being designed to about 200 to 250 bar.
In addition, the reactor with hydrogen recirculation conduit that found to operate is particularly advantageous.Therefore, can also extract except fatty alcohol obtain during hydrogenation short chain alcohol (such as when use fatty acid methyl ester time methyl alcohol), described short chain alcohol due to phase transformation from liquid phase be gas phase, with circulation hydrogen together be in gaseous form.
Particularly preferably be and provide cooling system in the recirculation of hydrogen, to make the condensation and can discharging from operation herein of extracted short chain alcohol.By mobile chemical equilibrium, this facilitates again the production of fatty alcohol conversely in addition.
Preferably, in order to measure the acid number (fatty acid ester) in mg (KOH)/g, described equipment is also included in the measuring apparatus in the container of reactor upstream, in the pipeline of reactor upstream or in reactor itself.Described measuring apparatus be such as original position running gas chromatograph (GC) or such as carrying out the infrared spectrometer of NIT or NIR, wherein infer acid number from measured parameter.By the value so measured, can to for introducing the dosing unit of alkali or the residence time in ion-exchanger controls, with the value making acid number be down to≤0.1mg (KOH)/g (fatty acid ester).
In preferred at one, before the hydrogenation, preferably after the content reducing the free fatty acids in reaction mixture, also stripping is carried out to reaction mixture.Thus the loss of catalyst activity owing to causing containing water can be avoided.
Further feature of the present invention, advantage and possible application can be obtained with reference to the accompanying drawings with the following explanation of exemplary.Described and/or illustrated all features itself or collectively form subject content of the present invention with any, independent of its in detail in the claims in perhaps its backward reference.
Accompanying drawing explanation
Fig. 1 illustrate for the production of fatty alcohol according to equipment of the present invention.
Embodiment
Fig. 1 illustrate for from fatty acid ester produce fatty alcohol according to equipment 1 of the present invention.Via pipeline 10, the reaction mixture containing at least one fatty acid ester, preferred fatty acid methyl esters and at least one free fatty acids is delivered in container 11, is then supplied to the reactor 20 for fatty acid ester described in hydrogenation.Container 11 comprises the instrument 12 amount of at least one free fatty acids contained in reaction mixture reduced.In the present invention's structure, this is ion-exchanger, but it also can be the device for adding alkali.Instrument 12 not only can be as directedly located in container 11, and in the pipeline 10 or 14 can being located at reactor 20 upstream or be directly connected with reactor 20.
By means of the acid number of measuring apparatus 13 assaying reaction mixture, the acid number of the reaction mixture wherein before hydrogenation should be about≤0.1mg (KOH)/g (fatty acid ester).In order to realize better mixing mutually, can stir container 11.
Via pipeline 14, the reaction mixture with the acid number of reduction is provided to stripping tower 15, and in described stripping tower 15, the water-content of reaction mixture reduces.When ester being heated to 220 DEG C, the water-content display of >100ppm is without obvious ester cracking.Copper catalyst such as catalyzer CU860 (BASF, at SiO
2on Cu) existence under, this catalyzer shows the obvious ester lytic activity at the temperature of 220 DEG C.
Via pipeline 15, then reaction mixture is introduced in reactor 20.Reactor 20 is designed to batch reactor and advantageously stirs with agitator 21.For preferred heterogeneous catalyst, particularly preferably in the hydrogenation carried out on copper catalyst at the temperature of 170 to 220 DEG C and 50 to 100 pressure clung to, supply of hydrogen.Via pipeline 27 and 28 and gas introducing apparatus 29 by hydrogen supply in reactor 20.
Hydrogen repeats itself is made via pipeline 24, cooling system 25 and pipeline 26 and 28.This tool has the following advantages: during hydrogenation obtain and the short chain alcohol partly existed in a gaseous form, particular methanol can carry out extracting via pipeline 24 together with hydrogen and cooling system 25 can be supplied to.In cooling system 25, then short chain alcohol, particularly methanol condensed are out, can lead back in reactor 20 to make the hydrogen of correspondingly purifying via pipeline 26 and 28 and gas introducing apparatus 29.Therefore, during reaction may remove short chain alcohol and reaction particularly advantageously carry out.Short chain alcohol in the application's meaning refers to the alcohol with the chain length being no more than five C atoms.
After completion of the reaction, can by system decompression in reactor 20, to make when using fatty acid methyl ester, the short chain alcohol during reaction obtained, i.e. methyl alcohol exist in a gaseous form and can extract in a gaseous form via pipeline 22.Via pipeline 23, gained fatty alcohol extracts in liquid form.Therefore significantly simplify the separation of alcohol.
EXPERIMENTAL EXAMPLE
Embodiment 1
In the autoclave stirred, carry out all experiments with batch reactions, wherein use the catalyzer/educt ratio of 0.273ml (catalyzer)/ml (educt) or 0.253g (catalyzer)/g (educt).Catalyst quality and catalyst volume refer to not reducing in CU860 used (BASF) the type copper catalyst extruding form, dried forms.Educt volume calculates based on its weight and the density at 15 DEG C.Before first time uses the catalyzer for the production of fatty alcohol, reducing program is carried out to described catalyzer, so that make it enter active condition.
Raw materials used is fatty acid methyl ester (the trade(brand)name SynativeES of the technical purity of BASF AG
), its composition forms primarily of Laurate methyl (about 75%) and Myristicin acid methylester (about 20%) and a small amount of rudimentary and higher fatty acid methyl esters.The density of this commerical prod at 15 DEG C is 860kg/t.The acid number of fatty acid methyl ester used is measured as 0.6mg (KOH)/g (fatty acid methyl ester).Moisture content is about 300ppm.
In order to be provided for the depickling raw material of comparative experiments, with ion-exchanger LewatitMP62 (BASF) to above-mentioned commerical prod SynativeES
process, so that make acid number be reduced to the value of 0.1mg (KOH)/g (fatty acid methyl ester).By the downstream stripping operation for removing reaction water with nitrogen, obtain the moisture content of about 100 to 150ppm.
Hydrogenation process carries out seven hours under the hydrogen pressure of 200 DEG C and 75 bar, and wherein each sample obtains from reaction mixture after 4 hours and after 7 hours.
Embodiment 1 discloses, in untreated fatty acid methyl ester, it is in fixing, that namely cost is obviously longer before the uniform catalyst activity time reaching previous untreated catalyzer, and it is from not reaching the conversion value reached with the reaction mixture of previous depickling.
Table 1 obviously illustrates that reaching fixing catalyst activity when use has the untreated raw material of the acid number of 0.6mg (KOH)/g (fatty acid methyl ester) has delay.When using depickling raw material, constant active is reached after three experiments (each experiment 7 hours=catalyst runs 21 hours), and when untreated raw material, only constant active can be observed after eight experiments (each experiment 7 hours=catalyst runs 56 hours).
In addition, when using reaction mixture pretreated according to the present invention, the obviously higher catalyst activity in transformation efficiency (U) form increased can be observed during first four hours:
Table 1: the transformation efficiency (U) depending on the fatty acid methyl ester (FAME) in reaction times
Can observe the catalyzer observed during the untreated raw material hydrogenation of copper-micro-red stain look form of product in the experiment of the complete series of carrying out utilizing untreated fatty acid methyl ester to leach, and do not observe completely in the experimentalists and technicians utilizing depickling raw material to carry out.
Embodiment 2
In the autoclave stirred, carry out all experiments in embodiment 2 with batch reactions, wherein use the catalyzer/educt ratio of 0.08ml (catalyzer)/ml (educt) or 0.1g (catalyzer)/g (educt).Catalyst quality and catalyst volume refer to not the reducing of CU860 used (BASF) the type copper catalyst of the form of extruding, dried forms.Educt volume calculates based on its weight and the density at 15 DEG C.Before using in first time the catalyzer being used for hydrogenated fat acid esters, reducing program is carried out to described catalyzer, so that make it enter active condition.
As educt, use octyl octanoate (98%) (Sigma-AldrichW281107).For this educt, mensuration acid number is 0.05mg (KOH)/g (fatty acid ester) and moisture content is about 200ppm.The density of commerical prod at 15 DEG C is 870kg/t.
For produce be used for comparative experiments containing acid starting material, be added into above-mentioned commerical prod W281107 by sad, so that be set in by acid number in 0.5mg (KOH)/g (fatty acid methyl ester) scope.During the seven hours hydrogenation process carried out under 200 DEG C and 75 bar hydrogen pressures, respectively in reaction mixture, obtain sample in starting point with after 1,3,5 and 7 hour.
Table 2: the time-histories depending on fatty acid ester (FAE) transformation efficiency of acid number (SZ)
Table 2 obviously illustrates, in the experiment utilizing lipid acid and the correspondingly acid number increase added, speed of reaction postpones.Due to compared to have 0.05mg (KOH)/g (fatty acid ester) acid number educt catalyst activity reduce, the transformation efficiency reached obviously declines.When use this be substantially free of acid raw material time, may observe that fatty acid ester becomes the transformation efficiency of 18% of corresponding fatty alcohol after one hour, and utilize add lipid acid comparative experiments in, can not measure significant transformation efficiency, it is 1.5%.Also observe, the acid number in reaction mixture obviously reduces in time, and namely contained free fatty acids disappears in reaction process.In conjunction with the catalyst activity reduced, also demonstrate that the result of study that the present invention is potential herein, according to described result of study, lipid acid occupies catalytic active center and therefore occurs that at least temporary transient catalyzer suppresses.
Reference numerals list
1 equipment
10 pipelines
11 containers
12 ion-exchangers
13 measuring apparatuss
14 pipelines
15 strippers
16 pipelines
20 reactors
21 agitators
22-24 pipeline
25 cooling systems
26-28 pipeline
29 gas introducing apparatus
Claims (15)
1. one kind for producing the method for fatty alcohol from the reaction mixture containing at least one fatty acid ester and at least one free fatty acids, be wherein at least one fatty alcohol with hydrogen by the hydrogenation of described at least one fatty acid ester, wherein under the pressure of the temperature of 150 DEG C to 300 DEG C and 50 bar to 250 bar, carry out described hydrogenation on a catalyst, it is characterized in that the content of the described at least one free fatty acids reduced before described hydrogenation in described reaction mixture.
2. method according to claim 1, it is characterized in that 170 to 220 DEG C temperature and/or 50 to 100 bar pressure under carry out described hydrogenation.
3. method according to claim 1 and 2, is characterized in that described catalyzer exists in solid form.
4. the method according to any one in aforementioned claim, is characterized in that described catalyzer is copper catalyst.
5. the method according to any one in aforementioned claim, is characterized in that the amount of described free fatty acids contained in described reaction mixture is reduced to the acid number of 0.1mg (KOH)/g (fatty acid ester).
6. the method according to any one in aforementioned claim, is characterized in that the content reducing described free fatty acids by adding alkali.
7. the method according to any one in claim 1 to 5, is characterized in that the content being reduced described free fatty acids by ion-exchanger.
8. the method according to any one in aforementioned claim, is characterized in that fatty acid methyl ester is used as fatty acid ester.
9. method according to claim 8, it is characterized in that after described hydrogenation completes, described pressure is brought down below the value of the dividing potential drop at the temperature that methyl alcohol is present in described reaction mixture after described hydrogenation completes, and extracts the methyl alcohol of residual volume in a gaseous form.
10. one kind for producing the equipment of fatty alcohol from the reaction mixture containing at least one fatty acid ester and at least one free fatty acids, described equipment comprises the reactor (20) for by the hydrogenation of described at least one fatty acid ester being at least one fatty alcohol on a catalyst, wherein said reactor is designed to the temperature of 150 to 300 DEG C and the pressure of 50 to 250 bar, and the gas introducing apparatus (29) comprised for introducing hydrogen, it is characterized in that at least one instrument (12) of the content for reducing the described at least one free fatty acids in described reaction mixture before described hydrogenation.
11. equipment according to claim 10, is characterized in that the instrument (12) using ion-exchanger or dosing unit as the content for reducing the described at least one free fatty acids in described reaction mixture.
12. equipment according to claim 10 or 11, is characterized in that described reactor (20) is designed to the hydrogenation under the pressure of the temperature of 170 to 220 DEG C and 50 to 100 bar.
13. according to claim 10 to the equipment described in any one in 12, it is characterized in that described reactor (20) is reactor or the batch reactor of running continuously.
14., according to claim 10 to the equipment described in any one in 13, is characterized in that described reactor (20) comprises the hydrogen recirculation conduit (24,26,28) with cooling system (25).
15. according to claim 10 to the equipment described in any one in 14, it is characterized in that described equipment comprises measuring apparatus (13) so that measure described reaction mixture in the acid number of mg (KOH)/g (fatty acid ester).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102014113197.5A DE102014113197A1 (en) | 2014-09-12 | 2014-09-12 | Process and plant for the production of fatty alcohols |
| DE102014113197.5 | 2014-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105418364A true CN105418364A (en) | 2016-03-23 |
Family
ID=54260716
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201520709612.8U Active CN205241567U (en) | 2014-09-12 | 2015-09-14 | A equipment for producing aliphatic alcohol |
| CN201510582697.2A Pending CN105418364A (en) | 2014-09-12 | 2015-09-14 | Process and plant for producing fatty alcohols |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201520709612.8U Active CN205241567U (en) | 2014-09-12 | 2015-09-14 | A equipment for producing aliphatic alcohol |
Country Status (6)
| Country | Link |
|---|---|
| CN (2) | CN205241567U (en) |
| BR (1) | BR112017004682B1 (en) |
| CO (1) | CO2017003062A2 (en) |
| DE (1) | DE102014113197A1 (en) |
| MY (1) | MY189114A (en) |
| WO (1) | WO2016037709A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108516924A (en) * | 2018-03-30 | 2018-09-11 | 江苏丰益化工科技有限公司 | A kind of production system for high-purity fatty alcohol |
| CN111801398A (en) * | 2018-02-21 | 2020-10-20 | 罗地亚经营管理公司 | Process for making secondary aliphatic alcohols, internal olefins, and internal olefin sulfonates |
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| CN1107756A (en) * | 1993-12-13 | 1995-09-06 | 花王株式会社 | Method for preparing copper-containing hydrogenation reaction catalyst and method for producing alcohol |
| US6187974B1 (en) * | 1998-03-11 | 2001-02-13 | Dhw Deutsche Hydrierwerke Gmbh Rodleben | Process for producing unsaturated fatty alcohols from lauric oils |
| US6313358B1 (en) * | 1998-04-23 | 2001-11-06 | Basf Aktiengesellschaft | Method for producing hexanediol |
| CN102076646A (en) * | 2009-04-07 | 2011-05-25 | 戴维加工技术有限公司 | Process for the co-production of a stream of a fatty alcohol having a first carbon chain length and a stream of a fatty alcohol having a second carbon length |
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| DE3246611A1 (en) * | 1982-12-16 | 1984-06-20 | Henkel KGaA, 4000 Düsseldorf | METHOD FOR PRODUCING ALCOHOL MIXTURES FROM EPOXIDIZED FATTY ALCOHOLS |
| DE4129622A1 (en) * | 1991-09-06 | 1993-03-11 | Henkel Kgaa | METHOD FOR PRODUCING UNSATURATED FATTY ALCOHOLS |
| DE4335781C2 (en) * | 1993-10-20 | 1998-02-19 | Henkel Kgaa | Vegetable-based fatty alcohols and process for their preparation |
| DE4425180C2 (en) * | 1994-07-16 | 1997-05-07 | Henkel Kgaa | Process for the production of unsaturated fatty alcohols or their esterified, alkoxylated and / or sulfated derivatives with improved low-temperature behavior |
| DE19712506C2 (en) * | 1997-03-25 | 2002-08-01 | Cognis Deutschland Gmbh | Process for the production of unsaturated fatty alcohols |
| JP3680948B2 (en) * | 2002-04-19 | 2005-08-10 | 新日本理化株式会社 | Liquid vegetable unsaturated alcohol and process for producing the same |
| GB201119871D0 (en) * | 2011-11-17 | 2011-12-28 | Davy Process Techn Ltd | Process |
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2014
- 2014-09-12 DE DE102014113197.5A patent/DE102014113197A1/en not_active Withdrawn
-
2015
- 2015-08-12 WO PCT/EP2015/025058 patent/WO2016037709A1/en active Application Filing
- 2015-08-12 BR BR112017004682-2A patent/BR112017004682B1/en active IP Right Grant
- 2015-08-12 MY MYPI2017700680A patent/MY189114A/en unknown
- 2015-09-14 CN CN201520709612.8U patent/CN205241567U/en active Active
- 2015-09-14 CN CN201510582697.2A patent/CN105418364A/en active Pending
-
2017
- 2017-03-29 CO CONC2017/0003062A patent/CO2017003062A2/en unknown
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| CN1107756A (en) * | 1993-12-13 | 1995-09-06 | 花王株式会社 | Method for preparing copper-containing hydrogenation reaction catalyst and method for producing alcohol |
| US6187974B1 (en) * | 1998-03-11 | 2001-02-13 | Dhw Deutsche Hydrierwerke Gmbh Rodleben | Process for producing unsaturated fatty alcohols from lauric oils |
| US6313358B1 (en) * | 1998-04-23 | 2001-11-06 | Basf Aktiengesellschaft | Method for producing hexanediol |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111801398A (en) * | 2018-02-21 | 2020-10-20 | 罗地亚经营管理公司 | Process for making secondary aliphatic alcohols, internal olefins, and internal olefin sulfonates |
| CN111801398B (en) * | 2018-02-21 | 2023-11-07 | 罗地亚经营管理公司 | Process for the manufacture of secondary aliphatic alcohols, internal olefins and internal olefin sulfonates |
| CN108516924A (en) * | 2018-03-30 | 2018-09-11 | 江苏丰益化工科技有限公司 | A kind of production system for high-purity fatty alcohol |
Also Published As
| Publication number | Publication date |
|---|---|
| DE102014113197A1 (en) | 2016-03-17 |
| CO2017003062A2 (en) | 2017-06-30 |
| WO2016037709A1 (en) | 2016-03-17 |
| BR112017004682B1 (en) | 2021-09-08 |
| BR112017004682A2 (en) | 2018-01-30 |
| CN205241567U (en) | 2016-05-18 |
| MY189114A (en) | 2022-01-26 |
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