CN105087084B - A kind of method of catalysis for preparing biodiesel oil - Google Patents
A kind of method of catalysis for preparing biodiesel oil Download PDFInfo
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- CN105087084B CN105087084B CN201410192855.9A CN201410192855A CN105087084B CN 105087084 B CN105087084 B CN 105087084B CN 201410192855 A CN201410192855 A CN 201410192855A CN 105087084 B CN105087084 B CN 105087084B
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- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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Abstract
The invention discloses a kind of method of catalysis for preparing biodiesel oil, this method includes making grease, monohydric alcohol and carboxylate haptoreaction, and the catalytic condition includes：Temperature≤300 DEG C, pressure is 0.1 10MPa, and the carboxylate is at least one of IV A races, I B races, II B races, IV B races, VII B races, VIII race and carboxylate of lanthanide metals.The method of the present invention can improve the yield of biodiesel, be additionally, since and use carboxylate as catalyst, and coordinate relatively low temperature and pressure, and the grease of high acid value and high impurity content is handled, and yield that still can be high prepares biodiesel.Meanwhile, in the method that the present invention is provided, it is not necessary to (such as pre-esterification processing) is pre-processed to the grease, so as to simplify the process for preparing biodiesel, therefore, substantially increase production efficiency.
Description
Technical field
The present invention relates to a kind of method of catalysis for preparing biodiesel oil.
Background technology
Biodiesel can carry out ester exchange reaction by grease and monohydric alcohol and be made, and have fatty acid ester in reaction product (i.e.
Biodiesel), also monoglyceride, two sweet esters, glycerine, and unreacted alcohol and grease (i.e. triglycerides).In the prior art
The preparation method of biodiesel can be divided into acid catalyzed process, base catalysis method, enzyme catalysis method and supercritical methanol technology.
CN1473907A uses the leftover bits and pieces and edible oil recovery of vegetable oil refining for raw material, catalyst by sulfuric acid, hydrochloric acid,
The inorganic acids such as p-methyl benzenesulfonic acid, DBSA, naphthalene sulfonic acids or organic acid compounding forms, acidified removal of impurities, continuous dehydration,
The processes such as esterification, layering, vacuum distillation are produced, and the pressure of continuous vacuum dehydration is 0.08-0.09MPa, temperature 60-95
DEG C, it is dehydrated to water content below 0.2%, esterif iotacation step catalyst charge 1-3%, 60-80 DEG C of esterification temperature, reaction time 6
Hour.Product first neutralizes removing catalyst after reaction, then, and layering removes water, goes product after water to obtain biology through vacuum distillation
Diesel oil.However, acid catalyzed reaction speed is slow, a large amount of spent acid are produced, environment is polluted.
In method disclosed in DE3444893, with acid catalyst, free fatty and alcohol, are carried out ester by normal pressure by 50-120 DEG C
Change, pre-esterification processing is carried out to oil plant, ester exchange reaction is then carried out under base metal catalysts, but the acid catalyst left will
Neutralized by alkali, the amount of base metal catalysts can increase.Using pre-esterification, make work flow elongated, equipment investment, energy consumption significantly on
Rise, in addition, base catalyst need to be removed from product, there are a large amount of waste water to produce, and more difficult recovery glycerine.
In method disclosed in US5713965A, in the presence of lipase, hexane makees solvent, and grease and alcohol reaction prepare fat
Fatty acid methyl esters, i.e. diesel fuel.
In method disclosed in CN1472280A, using fatty acid ester as acyl acceptor, in the presence of biology enzyme, catalysis life
Thing carries out transesterification reaction production biodiesel.The deficiency existed using enzyme catalyst is：Reaction time length, less efficient, enzyme is urged
Agent cost is higher, and the easy in inactivation in high purity methanol.
JP9905431 discloses a kind of method for preparing fatty acid ester by grease and monohydric alcohol reaction, and this method includes will
Methanol reacts to obtain fatty acid ester with grease, under the conditions of 270-280 DEG C, 11-12MPa, and fatty acid methyl ester production rate is 55-
60%, it can be seen that using continuous middle and high platen press, still suffer from the problem of fatty acid ester yield is relatively low.
The content of the invention
There is provided a kind of new biology for drawbacks described above in preparation method of the present invention in order to overcome existing biodiesel
The preparation method of diesel oil, this method technological process is simple, and improves under lower temperature and pressure the yield of biodiesel.
To achieve these goals, the invention provides a kind of method of catalysis for preparing biodiesel oil, this method includes making
Grease, monohydric alcohol and carboxylate haptoreaction, the catalytic condition include：Temperature≤300 DEG C, pressure is 0.1-
10MPa, the carboxylate is at least one in IV A races, I B races, II B races, IV B races, VII B races, VIII race and carboxylate of lanthanide metals
Kind.
The method of the present invention can improve the yield of biodiesel, be additionally, since and use carboxylate as catalyst, and match somebody with somebody
Relatively low temperature and pressure is closed, the grease of high acid value and high impurity content is handled, yield that still can be high prepares biology
Diesel oil.Meanwhile, in the method that the present invention is provided, it is not necessary to (such as pre-esterification processing) is pre-processed to the grease, so that
The process for preparing biodiesel is simplified, therefore, production efficiency is substantially increased.
Other features and advantages of the present invention will be described in detail in subsequent embodiment part.
Embodiment
The embodiment to the present invention is described in detail below.It should be appreciated that described herein specific
Embodiment is merely to illustrate and explain the present invention, and is not intended to limit the invention.
The method for the catalysis for preparing biodiesel oil that the present invention is provided includes making grease, monohydric alcohol and carboxylate haptoreaction,
The catalytic condition includes：Temperature≤300 DEG C, pressure is 0.1-10MPa, and the carboxylate is IV A races, I B races, II B
At least one of race, IV B races, VII B races, VIII race and carboxylate of lanthanide metals.
In the present invention, the grease can be various conventional greases, and its main component is fatty acid triglycercide, example
Such as, the grease can be at least one of for vegetable fat, animal fat and microbial grease, it can in addition contain being frying oil
And/or rotten waste oil.The vegetable fat can for example include soybean oil, rapeseed oil, peanut oil, sunflower seed oil, palm
Oil, coconut oil and come from fruit, stem, leaf, limb and the root of other various crops and wild plant and contain fat-based
Material (including the tall oil produced in paper-making process).Animal fat can for example include lard, butter, sheep oil, fish oil
Deng.
In the present invention, the monohydric alcohol can be monohydric alcohol of the carbon number between 1-6, can be saturated alcohols, also may be used
To be unsaturated alcohol.Under preferable case, the monohydric alcohol be methanol, ethanol, propyl alcohol, allyl alcohol, butanol and amylalcohol at least
One kind, more preferably methanol and/or ethanol.The propyl alcohol can be normal propyl alcohol and/or isopropanol, and the butanol can be
The isomers of n-butanol and/or n-butanol, the amylalcohol can be n-amyl alcohol and/or the isomers of n-amyl alcohol.
In the present invention, it can be carried as long as the grease and monohydric alcohol are contacted with carboxylate in aforementioned temperature and pressure limit
The yield of high biodiesel, and there is no particular limitation for the consumption of carboxylate.Under preferable case, relative to 100 parts by weight
Grease, the consumption of the carboxylate is 0.001-5 parts by weight.In the case of more preferably, relative to the grease of 100 parts by weight, institute
The consumption for stating carboxylate is 0.5-2 parts by weight.Most preferably, relative to the grease of 100 parts by weight, the consumption of the carboxylate is
0.6-1 parts by weight.
In the present invention, the carboxylate is IV A races, I B races, II B races, IV B races, VII B races, VIII race and lanthanide series metal carboxylic acid
At least one of salt.Preferably, the carboxylate be zinc polycarboxylate, ferric carboxylate, manganese carboxylate, carboxylic acid zirconium, cerium carboxylate, copper carboxylate,
At least one of at least one of carboxylic acids of lead and calcium carboxylates, more preferably zinc polycarboxylate, carboxylic acid zirconium and manganese carboxylate.
The carboxylate can be saturated carboxylic acid salt or salt unsaturated carboxylic acid, it is highly preferred that the carboxylate can
It is 1-30 carboxylate to think carbon number, and preferably carbon number is 7-20 carboxylate, and more preferably carbon number is 12-
20 carboxylate, most preferably octadecanoate (stearate), palmate (palmitate), Monoethanolamine Oleate (oleate) and
At least one of hexadecylene hydrochlorate (palm oil hydrochlorate).
According to further preferred embodiment of the present invention, the carboxylate is zinc octadecanate, stearic acid iron, stearic acid
Zirconium, stearic acid manganese, calcium stearate, hexadecylic acid zinc, hexadecylic acid iron, hexadecylic acid zirconium, hexadecylic acid manganese, hexadecylic acid calcium, octadecenic acid zinc,
Octadecenic acid iron, octadecenic acid zirconium, octadecenic acid manganese, octadecenic acid calcium, gaidic acid zinc, gaidic acid iron, gaidic acid zirconium,
At least one of gaidic acid manganese and gaidic acid calcium, most preferably, the carboxylate are zinc octadecanate, hexadecylic acid zinc, ten
Eight sour zirconiums, hexadecylic acid zirconium, stearic acid manganese, hexadecylic acid manganese, octadecenic acid zinc, gaidic acid zinc, octadecenic acid zirconium, gaidic acid
At least one of zirconium, octadecenic acid manganese and gaidic acid manganese.
In the present invention, when the consumption increase of the monohydric alcohol, the grease can be improved and be converted into aliphatic acid monohydric alcohol
The conversion ratio of ester, so as to improve the yield of biodiesel.Consider the cost and biodiesel of the production process of biodiesel
Yield, the weight ratio of the grease and monohydric alcohol can be 1：0.05-1, preferably 1：0.1-0.6, more preferably 1：0.2-
0.6。
In catalytic condition, temperature is higher, and reaction conversion ratio is higher, but temperature be higher than 300 DEG C when, reaction product
It is black, there is burnt matter to produce, meanwhile, also result in glycerine decomposition；Temperature is relatively low, and the yield of biodiesel can be reduced again, because
This, in foregoing temperature range, preferable temperature is 100-300 DEG C, more preferably 100-200 DEG C.Equally, pressure is improved to reaction
Favorably, but pressure is too high, the investment and operating cost for making device improve more, so, in foregoing pressure ranges, preferred pressure
For 0.1-5MPa, more preferably 0.1-2MPa.
The haptoreaction can carry out preparation and the satisfaction of biodiesel well known by persons skilled in the art
Carried out in the reactor of aforementioned temperature and pressure limit, the reactor can be tubular reactor, or still reaction
Device (such as autoclave).
When using tank reactor, the reactor preferably carries agitating device, so, is more beneficial for improving biological bavin
The yield of oil.When carrying out the haptoreaction of grease, monohydric alcohol and grease derivative, the grease, monohydric alcohol and grease derive
Thing can be supplied separately to reactor, provided after can also mixing and arrive reactor.
When using tubular reactor, grease and monohydric alcohol can be provided independently to reactor, or they are pre-mixed
After be supplied to reactor.Preferably, it is 0.1-20h-1 to control liquid hourly space velocity (LHSV).Before reactor is supplied to, preheater can be used
Material is preheated, reactor can also be directly entered.If using preheater, grease and monohydric alcohol can be preheated or mixed respectively
Preheat together afterwards.In tubular reactor, during grease and monohydric alcohol preferably enter tubular reactor from tubular reactor bottom, and
Reacting coarse product flows out from tubular reactor upper end.
In a preferred embodiment, the methods described that the present invention is provided also includes the mixing obtained after haptoreaction
Aliphatic acid unitary alcohol ester is isolated in thing, and (mixed ester phase contains fatty acid ester, monoglyceride, two sweet esters and unreacted glycerine three
Ester etc.), the method for the separation can be implemented using conventional separation method, for example can be real using the method for vacuum distillation
It is existing.
In further preferred embodiment, the methods described that the present invention is provided is additionally included in be obtained after haptoreaction
Mixture in isolate aliphatic acid unitary alcohol ester before isolate monohydric alcohol.The method for separating monohydric alcohol can be using routine
Method (as distilled) is realized.The monohydric alcohol isolated can be recycled.
In preferred embodiment, the method that the present invention is provided is additionally included in the mixture obtained after haptoreaction
In isolate after monohydric alcohol and before aliphatic acid unitary alcohol ester is isolated, isolate glycerine.The method for separating glycerine can be with
Realized, for example, can be realized by the method for sedimentation separation using conventional method.The glycerine isolated can be recycled profit
With.
According to the method that provides of the present invention, to the acid number of the grease, there is no particular limitation, for example, can be 0.1-
200mg KOH/g.The method of the present invention can also be prepared when carrying out haptoreaction using the grease of high acid value with higher yields
Biodiesel, therefore, the acid number of the grease can be 60-200mgKOH/g, more preferably 90-200mg KOH/g." acid number "
Refer to the milligram number for neutralizing potassium hydroxide needed for free fatty in 1g greases under test conditions, according to GB/T5530-1998
Indicator method in standard is measured.
The present invention is described in detail by the following examples.The raw material used in embodiment, unless stated otherwise,
For commercially available prod.And in the examples below, the yield of biodiesel is calculated by following formula：
The yield of biodiesel=(quality of quality/grease of the biodiesel finally obtained) × 100%.
Embodiment 1
By the soybean oil that 100g acid numbers are 0.9mg KOH/g, 17g methanol and 1.7g zinc octadecanates add autoclave together
In, under conditions of 200 revs/min of 140 DEG C of temperature, pressure 0.7MPa and mixing speed, react 1.5 hours, obtain reacting thick production
Thing.Reacting coarse product is distilled, methanol is removed under conditions of 150 DEG C of bottom ＜, and methanol is reclaimed and repeated
Use, leftover materials are isolated after glycerine phase, vacuum distillation is mutually carried out to obtained mixed ester, it is biological bavin to steam material
Oil, the yield of biodiesel is 83.9%.
Embodiment 2
100g acid numbers are added into autoclave together for 1.7mg KOH/g rapeseed oil, 17g methanol and 1.7g zinc octadecanates
In, under conditions of 200 revs/min of 140 DEG C of temperature, pressure 0.7MPa and mixing speed, react 1.5 hours, obtain reacting thick production
Thing.Reacting coarse product is distilled, methanol is removed under conditions of 150 DEG C of bottom ＜, and methanol is reclaimed and repeated
Use, leftover materials are isolated after glycerine phase, vacuum distillation is mutually carried out to obtained mixed ester, it is biological bavin to steam material
Oil, the yield of biodiesel is 84.7%.
Embodiment 3
By the waste grease that 100g acid numbers are 91mg KOH/g, 17g methanol and 0.7g hexadecylic acid zirconiums add high pressure together
In kettle, under conditions of 200 revs/min of 140 DEG C of temperature, pressure 0.7MPa and mixing speed, react 1.5 hours, obtain reaction thick
Product.Reacting coarse product is distilled, methanol is removed under conditions of 150 DEG C of bottom ＜, and methanol is reclaimed and again
Use again, leftover materials are isolated after glycerine phase, vacuum distillation is mutually carried out to obtained mixed ester, it is biological bavin to steam material
Oil, the yield of biodiesel is 92.3%.
Embodiment 4
By the waste grease that 100g acid numbers are 40mg KOH/g, 17g methanol and 0.7g octadecenic acids manganese (manganese oleate) one
Rise in addition autoclave, under conditions of 200 revs/min of 140 DEG C of temperature, pressure 0.7MPa and mixing speed, react 1.5 hours,
Obtain reacting coarse product.Reacting coarse product is distilled, methanol is removed under conditions of 150 DEG C of bottom ＜, and methanol is entered
Row is reclaimed and reused, and leftover materials are isolated after glycerine phase, vacuum distillation is mutually carried out to obtained mixed ester, steams material
As biodiesel.The yield of biodiesel is 84.4%.
Embodiment 5
By the sunflower oil that 100g acid numbers are 0.4mg KOH/g, 17g methanol and 0.9g stearic acid iron add high pressure together
In kettle, under conditions of 200 revs/min of 130 DEG C of temperature, pressure 0.6MPa and mixing speed, react 2 hours, obtain reacting thick production
Thing.Reacting coarse product is distilled, methanol is removed under conditions of 150 DEG C of bottom ＜, and methanol is reclaimed and repeated
Use, leftover materials are isolated after glycerine phase, vacuum distillation is mutually carried out to obtained mixed ester, it is biological bavin to steam material
Oil, the yield of biodiesel is 49.9%.
Comparative example 1
Biodiesel is prepared according to the method for embodiment 5, unlike, without stearic acid iron, the yield of biodiesel
For 2.7%.
Comparative example 2
By the sunflower oil that 100g acid numbers are 0.4mg KOH/g, 25g methanol and 4g aluminium distearates add high pressure together
In kettle, under conditions of 400 revs/min of 160 DEG C of temperature, pressure 1.2MPa and mixing speed, react 4 hours, obtain reacting thick production
Thing.Reacting coarse product is distilled, methanol is removed under conditions of 150 DEG C of bottom ＜, and methanol is reclaimed and repeated
Use, leftover materials are isolated after glycerine phase, vacuum distillation is mutually carried out to obtained mixed ester, it is biological bavin to steam material
Oil, the yield of biodiesel is 6%.
Embodiment 6
Using waste grease that acid number is 7mg KOH/g as raw material, compare 0.2, liquid hourly space velocity (LHSV) 1.2h-1 bar in alcohol oil quality
Under part, grease and methanol are continuously provided in tubular reactor, add the stearic acid that weight is grease weight 0.15%
The hexadecylic acid calcium of iron and grease weight 0.05%, it is 260 DEG C to control temperature in reactor, and pressure is 6MPa, reacting coarse product warp
Unreacted methanol is distilled out, standing separation glycerine phase, rectification under vacuum mixed ester phase steams material as biodiesel, biological bavin
The yield 85.1% of oil.
Embodiment 7
Using soybean oil that acid number is 0.6mg KOH/g as raw material, compare 0.2, liquid hourly space velocity (LHSV) 1.2h-1 bar in alcohol oil quality
Under part, oil and methanol are continuously provided in tubular reactor, add the octadecenic acid zinc that weight is grease weight 0.2%
(zinc oleate), it is 260 DEG C to control temperature in reactor, and pressure is 6MPa, and reacting coarse product is quiet through distilling out unreacted methanol
Separation glycerine phase is put, vacuum distillation mixed ester phase steams material as biodiesel, the yield 81% of biodiesel.
As can be seen from the above embodiments, method of the invention can significantly improve the yield of biodiesel.Especially, it is right
The amount and reaction condition of the carboxylate used in ratio 2 are superior to embodiment 5, but the yield of biodiesel is far below embodiment
5, illustrate that specific carboxylate can significantly improve biological bavin as catalyst progress haptoreaction only using in the present invention
The yield of oil.
The preferred embodiment of the present invention described in detail above, still, the present invention are not limited in above-mentioned embodiment
Detail, in the range of the technology design of the present invention, a variety of simple variants can be carried out to technical scheme, this
A little simple variants belong to protection scope of the present invention.
It is further to note that each particular technique feature described in above-mentioned embodiment, in not lance
In the case of shield, can be combined by any suitable means, in order to avoid unnecessary repetition, the present invention to it is various can
The combination of energy no longer separately illustrates.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally
The thought of invention, it should equally be considered as content disclosed in this invention.
Claims (13)
1. a kind of method of catalysis for preparing biodiesel oil, it is characterised in that this method includes connecing grease, monohydric alcohol and carboxylate
Reaction is touched, the catalytic condition includes：Temperature≤300 DEG C, pressure is 0.1-10MPa, and the carboxylate is IV B races gold
Belong at least one of carboxylate, wherein, relative to the grease of 100 parts by weight, the consumption of the carboxylate is 0.001-5 weight
Part, the weight ratio of the grease and monohydric alcohol is 1：0.05-0.2.
2. according to the method described in claim 1, wherein, relative to the grease of 100 parts by weight, the consumption of the carboxylate is
0.5-2 parts by weight.
3. method according to claim 1 or 2, wherein, the carboxylate is carboxylic acid zirconium.
4. method according to claim 1 or 2, wherein, the carboxylate be carbon number be 1-30 carboxylate.
5. method according to claim 1 or 2, wherein, the carboxylate be carbon number be 7-20 carboxylate.
6. method according to claim 1 or 2, wherein, the carboxylate is octadecanoate, palmate, octadecenic acid
At least one of salt and hexadecylene hydrochlorate.
7. method according to claim 1 or 2, wherein, the carboxylate is stearic acid zirconium, hexadecylic acid zirconium, octadecenic acid
At least one of zirconium and gaidic acid zirconium.
8. according to the method described in claim 1, wherein, the weight ratio of the grease and monohydric alcohol is 1：0.05-0.1.
9. according to the method described in claim 1, wherein, the catalytic condition includes：Temperature is 100-300 DEG C, pressure
Power is 0.1-5MPa.
10. the method according to claim 1 or 9, wherein, the catalytic condition includes：Temperature is 100-200
DEG C, pressure is 0.1-2MPa.
11. according to the method described in claim 1, wherein, the acid number of the grease is 0.1-200mg KOH/g.
12. according to the method described in claim 1, wherein, the acid number of the grease is 60-200mg KOH/g.
13. according to the method described in claim 1, wherein, the acid number of the grease is 90-200mg KOH/g.
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| CN109423359B (en) * | 2017-08-30 | 2022-03-11 | 中国石油化工股份有限公司 | Method for stably preparing biodiesel |
| CN109971553A (en) * | 2017-12-27 | 2019-07-05 | 中国石油化工股份有限公司 | A method of improving biodiesel yield |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1923990A (en) * | 2005-08-31 | 2007-03-07 | 中国石油化工股份有限公司 | Process for preparing fatty acid ester |
| CN102337182A (en) * | 2010-07-23 | 2012-02-01 | 中国石油化工股份有限公司 | Preparation method of biodiesel |
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2014
- 2014-05-08 CN CN201410192855.9A patent/CN105087084B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1923990A (en) * | 2005-08-31 | 2007-03-07 | 中国石油化工股份有限公司 | Process for preparing fatty acid ester |
| CN102337182A (en) * | 2010-07-23 | 2012-02-01 | 中国石油化工股份有限公司 | Preparation method of biodiesel |
Non-Patent Citations (1)
| Title |
|---|
| Synthesis of biodiesel via homogeneous Lewis acid catalyst;M. Di Serio，et al.;《Journal of Molecular Catalysis A: Chemical》;20050719(第239期);第111-115页 * |
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