CN104262088A - Method for synthesizing isopropanol from acetic acid - Google Patents

Method for synthesizing isopropanol from acetic acid Download PDF

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Publication number
CN104262088A
CN104262088A CN201410433288.1A CN201410433288A CN104262088A CN 104262088 A CN104262088 A CN 104262088A CN 201410433288 A CN201410433288 A CN 201410433288A CN 104262088 A CN104262088 A CN 104262088A
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China
Prior art keywords
virahol
acetic acid
catalyzer
acetic
dryness
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CN201410433288.1A
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Chinese (zh)
Inventor
李德宝
鲁怀乾
肖勇
贾丽涛
侯博
阿从标
林明桂
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Shanxi Institute of Coal Chemistry of CAS
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Shanxi Institute of Coal Chemistry of CAS
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Publication of CN104262088A publication Critical patent/CN104262088A/en
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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
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal

Abstract

The invention provides a method for synthesizing isopropanol from acetic acid. The method is used for synthesizing isopropanol by reacting the raw material acetic acid with hydrogen in a fixed bed reactor filled with a catalyst under the reaction conditions of a reaction temperature in the range of 200-350 DEG C, pressure in the range of 0.5-4.0MPa, the space velocity of the acetic acid liquid in the range of 0.1 to 2.0 per hour and the mol ratio of the acetic acid to the hydrogen of 1:(1-10). The method for synthesizing the isopropanol from the acetic acid has the advantages of low production cost, simple process, and high acetic acid conversion rate and isopropanol selectivity.

Description

A kind of method of acetic synthesis Virahol
Technical field
The invention belongs to a kind of method of acetic synthesis Virahol.
Background technology
Virahol is as being a kind of important Chemicals and raw material, and its purposes main is solvent and synthetic intermediate.Asia is the second largest Virahol consumption market being only second to North America, in China's annual Virahol consumption rate of growth up to 10%, particularly powerful in the growth of ink and paint field.At present, Virahol is mainly through propylene hydration method and the two kinds of operational path preparations of acetone hydrogenation method; Patent CN 20121034990 provides a kind of propylene and prepare Virahol in the solvent containing polyethylene glycol nonylphenyl ether, Triton X-100, N-Methyl pyrrolidone, and the transformation efficiency of propylene is about 60-80%, and the selection type of Virahol is greater than 90%.Provide a kind of method of acetone liquid-phase hydrogenatin preparing isopropanol in patent CN103030527A, under 1.0-5.0MPa, 120-200 DEG C of reaction conditions, the transformation efficiency of acetone is greater than 90%, and the selectivity of Virahol is greater than 80%.In patent CN103539635A, in the presence of hydrogen, take acetone as raw material, answering temperature to be 80-180 DEG C, pressure is 1.0-4.0MPa, and the air speed of acetone is 0.1-5h -1, the mol ratio of acetone and hydrogen is under the condition of 1:1-4, and containing in the fixed-bed reactor of catalyzer, acetone and hydrogen reaction generate Virahol, and acetone conversion is greater than 95%, and the selectivity of Virahol is greater than 85%.But the raw material propylene of two kinds of approach and acetone all have strong dependence for petroleum resources, soaring along with oil price in recent years, makes to produce the basis that Virahol becomes more and more higher, therefore develops to prepare Virahol by comparatively cheap raw material and just seem particularly necessary.
Summary of the invention
The object of this invention is to provide that a kind of production cost is low, technique be simple, acetic acid transformation efficiency and the high method being prepared Virahol by acetic acid of Virahol selectivity.
Technical scheme provided by the present invention is as follows: in the presence of hydrogen, take acetic acid as raw material, temperature of reaction be 200-350 DEG C, pressure is 0.5-4.0MPa, acetic acid liquid air speed is 0.1-2.0h -1, acetic acid and hydrogen mol ratio be under the reaction conditions of 1:1-10, by the fixed-bed reactor of loading catalyst, acetic acid and hydrogen reaction generate Virahol.
The invention provides consisting of of catalyzer: with the percent by weight of catalyzer, the content of rare earth oxide carrier is 65-90%, and the content of transition metal oxide is 5%-30%, and the content of alkalimetal oxide auxiliary agent is 0.5-5%.
Rare earth oxide described above comprises oxide compound wherein one or more such as La, Ce, Pr, Nd, Pm, Sm or Eu.
Transition metal oxide described above comprises Fe, Co, Ni, Mn, V or Cu metal oxide etc.
Alkalimetal oxide described above comprises the oxide compound of the metals such as Li, Na, K, Ru or Cs.
The preparation method of catalyzer of the present invention is:
(1) take soluble ree nitrate and be dissolved in deionized water, be configured to the aqueous solution of 0.1-0.5M, be then metal ion in molar ratio: coordination agent=1:1-8 adds coordination agent, be placed in 65-90 DEG C of stirred in water bath evaporate to dryness, sample after evaporate to dryness is warming up to 450-800 DEG C of roasting 2-12h with 0.5-5 DEG C/min, obtains support of the catalyst;
(2) precursor salt of soluble transition metal oxide compound is dissolved in deionized water, be configured to the aqueous solution of 0.1-2M, by the composition of catalyzer, the aqueous solution is joined in the carrier obtained in step (1), in 65-90 DEG C of stirred in water bath evaporate to dryness after standing 3-10h, the sample after evaporate to dryness dries 6-48h in 80-120 DEG C;
(3) by the composition of catalyzer, taking basic metal precursor salt joins in the sample obtained in step (2), after grinding 0.5-6h, is 0.5-5 DEG C/min by obtained sample with temperature rise rate, be warming up to 450-800 DEG C of roasting 4-24h, after being cooled to room temperature, obtain catalyzer.
The precursor of transition metal oxide described above comprises nitrate, the acetate and ammonium meta-vanadate etc. of Fe, Co, Ni, Mn, Cu; Basic metal precursor comprises the nitrate, carbonate etc. of Li, Na, K, Rb, Cs.
Coordination agent as above comprises citric acid, ammonium citrate, ethylenediamine tetraacetic acid (EDTA) (EDTA), cetyl trimethylammonium bromide (CTAB), sodium lauryl sulphate (SDS), disodium ethylene diamine tetraacetate (Na 2eDTA) etc.
Catalyzer provided by the invention has the following advantages:
(1) preparation process of catalyzer is simple, and reactive behavior is high.Under the reaction conditions optimized, the transformation efficiency of acetic acid can reach more than 95%, and Virahol selectivity reaches more than 60%.
(2) reaction conditions is gentle, is applicable to industrial mass production, extremely low compared to its cost of noble metal hydrogenation catalyst.
(3) adopt catalyzer provided by the present invention, acetic acid improves compared to its economic worth of raw material greatly through reacted principal product and Main By product, and therefore economic worth is high, has good industrial application value.
Embodiment
Below in conjunction with specific embodiment, the content arrived involved in the present invention is described, but concrete embodiment is not below construed as limiting the invention, but further instruction.
Embodiment 1
(1) a certain amount of Ce (NO is taken 3) 46H 2o is dissolved in deionized water, is configured to the aqueous solution of 0.2M, then Ce in molar ratio 4+: citric acid=1:3 takes a certain amount of citric acid and joins Ce (NO 3) 6H 2in the aqueous solution of O, and be placed on 65 DEG C of stirred in water bath evaporates to dryness.The sample obtained is in 800 DEG C of roasting 10h, and heat-up rate is 1 DEG C/min.After being cooled to room temperature, sample be support of the catalyst.
(2) 100g Fe (NO is taken 3) 39H 2o, is configured to the aqueous solution of 0.5M.The carrier synthesized before taking 5g is 30% by the load quality mark of ferric oxide, pipettes the Fe (NO of certain volume 3) 39H 2the O aqueous solution adds in carrier, and standing 5h is placed on 90 DEG C of stirred in water bath evaporates to dryness.Sample after evaporate to dryness is placed in 80 DEG C of baking oven 24h.
(3) by K 2the massfraction of O load is 5% K taking certain mass 2cO 3joining institute in (2) obtains in sample, after grinding 6h by sample be warming up to 500 DEG C of roasting 8h with 2 DEG C/min.After being cooled to room temperature, be obtained finished catalyst A.
The mass percent of obtained each component of catalyzer is: support C eO 2content is 65%, transition metal oxide Fe 2o 3content be 30%, basic metal K 2the content of O is 5%.
Catalyst A is loaded in fixed-bed reactor, passes into acetic acid and hydrogen, 200 DEG C, 4.0MPa, acetic acid and hydrogen mol ratio be: 1:4, the air speed of acetic acid is 0.1h -1reaction conditions under, the performance of evaluate catalysts, experimental result is in table 1.
Embodiment 2
Catalyst A in embodiment 1 is loaded in fixed-bed reactor, passes into acetic acid and hydrogen, 350 DEG C, 4.0MPa, acetic acid and hydrogen mol ratio be: 1:10, the air speed of acetic acid is 0.1h -1reaction conditions under, the performance of evaluate catalysts, experimental result is in table 1.
Embodiment 3
(1) a certain amount of Ce (NO is taken 3) 46H 2o and Sm (NO 3) 36H 2o is dissolved in deionized water, and be configured to the aqueous solution that concentration of metal ions is 0.3M, wherein Ce and Sm mol ratio is 1:1.(Ce in molar ratio 4++ Sm 3+): citric acid=1:8 takes a certain amount of citric acid and joins in rare earth nitrate aqueous solution.The solution that obtains is placed in 90 DEG C of stirred in water bath evaporates to dryness.Sample after evaporate to dryness is placed in retort furnace and is warming up to 600 DEG C of roasting 10h with 0.5 DEG C/min, obtains support of the catalyst.
(2) 100g Co (NO is taken 3) 26H 2o, is configured to the aqueous solution of 0.1M.The carrier synthesized before taking 5g is 10% by the load quality mark of cobalt oxide, pipettes the Co (NO of certain volume 3) 26H 2the O aqueous solution adds in carrier, and standing 3h is placed on 75 DEG C of stirred in water bath evaporates to dryness.Sample after evaporate to dryness is placed in 120 DEG C of baking oven 6h.
(3) by Cs 2the charge capacity of O is 0.5% take a certain amount of CsNO 3join in the sample obtained in (2), after grinding 0.5h, obtained sample is placed in retort furnace and is warming up to 750 DEG C of roasting 12h with 1 DEG C/min, after being cooled to room temperature, be obtained catalyst B.
The mass percent of obtained each component of catalyzer: carrier (CeO 2+ Sm 2o 3) be 89.5%, Co 4o 3be 10%, alkaline assistant Cs 2o content is 0.5%.
Catalyst B is loaded in fixed-bed reactor, passes into acetic acid and hydrogen, 220 DEG C, 1.5MPa, acetic acid and hydrogen mol ratio be 1:8, the air speed of acetic acid is 1.0h -1reaction conditions under, the acetic acid Hydrogenation Virahol performance of evaluate catalysts, experimental result is in table 1.
Embodiment 4
Catalyst B in embodiment 3 is loaded in fixed-bed reactor, passes into acetic acid and hydrogen, 300 DEG C, 2.5MPa, acetic acid and hydrogen mol ratio be: 1:5, the air speed of acetic acid is 1.5h -1reaction conditions under, the performance of evaluate catalysts, experimental result is in table 1.
Embodiment 5
(1) a certain amount of Eu (NO is taken 3) 36H 2o is dissolved in deionized water, is configured to the aqueous solution that concentration of metal ions is 0.5M, Eu in molar ratio 3+: EDTA=1:8 takes a certain amount of EDTA and joins in rare earth nitrate aqueous solution.The solution that obtains is placed in 90 DEG C of stirred in water bath evaporates to dryness.Sample after evaporate to dryness is placed in retort furnace and is warming up to 600 DEG C of roasting 10h with 0.5 DEG C/min, obtains support of the catalyst.
(2) 100g Ni (NO is taken 3) 26H 2o, is configured to the aqueous solution of 2M.The carrier synthesized before taking 5g is 15% by the load quality mark of nickel oxide, pipettes the Ni (NO of certain volume 3) 26H 2the O aqueous solution adds in carrier, and standing 10h is placed on 75 DEG C of stirred in water bath evaporates to dryness.Sample after evaporate to dryness is placed in 80 DEG C of baking oven 24h.
(3) by Li 2the charge capacity of O is 0.5% take a certain amount of LiNO 3join in the sample obtained in (2), after grinding 3h, obtained sample is placed in retort furnace and is warming up to 600 DEG C of roasting 10h with 5 DEG C/min, after being cooled to room temperature, be obtained catalyzer C.
The mass percent of obtained each component of catalyzer: carrier Eu 2o 3be 84.5%, NiO be 15%, alkaline assistant Cs 2o content is 0.5%.
Catalyzer C is loaded in fixed-bed reactor, passes into acetic acid and hydrogen, 300 DEG C, 2.5MPa, acetic acid and hydrogen mol ratio be 1:1, the air speed of acetic acid is 2.0h -1reaction conditions under, the acetic acid Hydrogenation Virahol performance of evaluate catalysts, experimental result is in table 1.
Embodiment 6
(1) a certain amount of Pr (NO is taken 3) 36H 2o is dissolved in deionized water, is configured to the aqueous solution that concentration of metal ions is 0.25M, Pr in molar ratio 3+: SDS=1:6 takes a certain amount of SDS and joins in rare earth nitrate aqueous solution.The solution that obtains is placed in 75 DEG C of stirred in water bath evaporates to dryness.Sample after evaporate to dryness is placed in retort furnace and is warming up to 700 DEG C of roasting 8h with 5 DEG C/min, obtains support of the catalyst.
(2) 100g NH is taken 4vO 3, be configured to the aqueous solution of 1M.The carrier synthesized before taking 5g, by V 2o 5load quality mark be 25%, pipette the NH of certain volume 4vO 3the aqueous solution adds in carrier, and standing 6h is placed on 85 DEG C of stirred in water bath evaporates to dryness.Sample after evaporate to dryness is placed in 110 DEG C of baking oven 7.5h.
(3) by Na 2the charge capacity of O is 3% take a certain amount of NaNO 3join in the sample obtained in (2), after grinding 2.5h, obtained sample is placed in retort furnace and is warming up to 550 DEG C of roasting 20h with 3 DEG C/min, after being cooled to room temperature, be obtained catalyzer D.
The mass percent of obtained each component of catalyzer D: carrier Pr 2o 3be 72%, V 2o 5be 25%, alkaline assistant Na 2o content is 3%.
Catalyzer D is loaded in fixed-bed reactor, passes into acetic acid and hydrogen, 200 DEG C, 1.8MPa, acetic acid and hydrogen mol ratio be 1:5, the air speed of acetic acid is 0.8h -1reaction conditions under, the acetic acid Hydrogenation Virahol performance of evaluate catalysts, experimental result is in table 1.
Embodiment 7
(1) La in molar ratio 3+: Ce 3+=2:1 takes a certain amount of La (NO 3) 36H 2o and Ce (NO 3) 36H 2o is dissolved in deionized water, is configured to the aqueous solution that concentration of metal ions is 0.15M, (La in molar ratio 3++ Ce +): CTAB=1:3 takes a certain amount of CTAB and joins in rare earth nitrate aqueous solution.The solution that obtains is placed in 90 DEG C of stirred in water bath evaporates to dryness.Sample after evaporate to dryness is placed in retort furnace and is warming up to 500 DEG C of roasting 6h with 1.5 DEG C/min, obtains support of the catalyst.
(2) 100gCu (NO is taken 3) 23H 2o, is configured to the aqueous solution of 0.8M.The carrier synthesized before taking 5g is 8% by the load quality mark of CuO, pipettes the Cu (NO of certain volume 3) 23H 2the O aqueous solution adds in carrier, and standing 10h is placed on 70 DEG C of stirred in water bath evaporates to dryness.Sample after evaporate to dryness is placed in 90 DEG C of baking oven 40h.
(3) by Rb 2the charge capacity of O is 1.5% take a certain amount of RbNO 3join in the sample obtained in (2), after grinding 4h, obtained sample is placed in retort furnace and is warming up to 500 DEG C of roasting 12h with 3 DEG C/min, after being cooled to room temperature, be obtained catalyzer E.
The mass percent of obtained each component of catalyzer E: carrier (La 2o 3+ CeO 2) be 91.5%, CuO be 8%, alkaline assistant Rb 2o content is 1.5%.
Catalyzer E is loaded in fixed-bed reactor, passes into acetic acid and hydrogen, 280 DEG C, 3.2MPa, acetic acid and hydrogen mol ratio be 1:7, the air speed of acetic acid is 1.2h -1reaction conditions under, the acetic acid Hydrogenation Virahol performance of evaluate catalysts, experimental result is in table 1.
Embodiment 8
(1) a certain amount of Sm (NO is taken 3) 36H 2o is dissolved in deionized water, is configured to the aqueous solution that concentration of metal ions is 0.4M, Sm in molar ratio 3+: EDTA=1:6 takes a certain amount of EDTA and joins in the aqueous solution of rare earth nitrate.The solution that obtains is placed in 85 DEG C of stirred in water bath evaporates to dryness.Sample after evaporate to dryness is placed in retort furnace and is warming up to 600 DEG C of roasting 4h with 3.5 DEG C/min, obtains support of the catalyst.
(2) 100gFe (NO is taken 3) 39H 2o, is configured to the aqueous solution of 1.5M.The carrier synthesized before taking 5g, by Fe 2o 3load quality mark be 8%, pipette the Fe (NO of certain volume 3) 39H 2the O aqueous solution adds in carrier, and standing 5h is placed on 80 DEG C of stirred in water bath evaporates to dryness.Sample after evaporate to dryness is placed in 120 DEG C of baking oven 48h.
(3) by Cs 2the charge capacity of O is 0.8% take a certain amount of CsNO 3join in the sample obtained in (2), after grinding 5.5h, obtained sample is placed in retort furnace and is warming up to 450 DEG C of roasting 10h with 5 DEG C/min, after being cooled to room temperature, be obtained catalyzer F.
The mass percent of obtained each component of catalyzer F: carrier S m 2o 3be 91.2%, Fe 2o 3be 8%, alkaline assistant Cs 2o content is 0.8%.
Catalyzer F is loaded in fixed-bed reactor, passes into acetic acid and hydrogen, 350 DEG C, 4.0MPa, acetic acid and hydrogen mol ratio be 1:10, the air speed of acetic acid is 0.5h -1reaction conditions under, the acetic acid Hydrogenation Virahol performance of evaluate catalysts, experimental result is in table 1.
Table 1 acetic acid Hydrogenation isopropanol reaction performance table

Claims (9)

1. a method for acetic synthesis Virahol, is characterized in that comprising the steps:
In the presence of hydrogen, take acetic acid as raw material, temperature of reaction be 200-350 DEG C, pressure is 0.5-4.0MPa, acetic acid liquid air speed is 0.1-2.0h -1, acetic acid and hydrogen mol ratio be under the reaction conditions of 1:1-10, by the fixed-bed reactor of loading catalyst, acetic acid and hydrogen reaction generate Virahol.
2. the method for a kind of acetic synthesis Virahol as claimed in claim 1, it is characterized in that consisting of of described catalyzer: with the percent by weight of catalyzer, the content of rare earth oxide carrier is 65-90%, the content of transition metal oxide is 5%-30%, and the content of alkalimetal oxide auxiliary agent is 0.5-5%.
3. the method for a kind of acetic synthesis Virahol as claimed in claim 2, is characterized in that one or more that described rare earth oxide comprises in La, Ce, Pr, Nd, Pm, Sm or Eu oxide compound.
4. the method for a kind of acetic synthesis Virahol as claimed in claim 2, is characterized in that described transition metal oxide comprises Fe, Co, Ni, Mn, V or Cu metal oxide.
5. the method for a kind of acetic synthesis Virahol as claimed in claim 2, is characterized in that described alkalimetal oxide comprises the oxide compound of Li, Na, K, Ru or Cs metal.
6. the method for a kind of acetic synthesis Virahol as described in any one of claim 2-5, is characterized in that the preparation method of catalyzer comprises the steps:
(1) take soluble ree nitrate and be dissolved in deionized water, be configured to the aqueous solution of 0.1-0.5M, be then metal ion in molar ratio: coordination agent=1:1-8 adds coordination agent, be placed in 65-90 DEG C of stirred in water bath evaporate to dryness, sample after evaporate to dryness is warming up to 450-800 DEG C of roasting 2-12h with 0.5-5 DEG C/min, obtains support of the catalyst;
(2) precursor salt of soluble transition metal oxide compound is dissolved in deionized water, be configured to the aqueous solution of 0.1-2M, by the composition of catalyzer, the aqueous solution is joined in the carrier obtained in step (1), in 65-90 DEG C of stirred in water bath evaporate to dryness after standing 3-10h, the sample after evaporate to dryness dries 6-48h in 80-120 DEG C;
(3) by the composition of catalyzer, taking basic metal precursor salt joins in the sample obtained in step (2), after grinding 0.5-6h, is 0.5-5 DEG C/min by obtained sample with temperature rise rate, be warming up to 450-800 DEG C of roasting 4-24h, after being cooled to room temperature, obtain catalyzer.
7. the method for a kind of acetic synthesis Virahol as claimed in claim 6, is characterized in that the precursor of described transition metal oxide comprises the nitrate of Fe, Co, Ni, Mn, Cu, acetate and ammonium meta-vanadate.
8. the method for a kind of acetic synthesis Virahol as claimed in claim 6, is characterized in that described basic metal precursor comprises nitrate or the carbonate of Li, Na, K, Rb, Cs.
9. the method for a kind of acetic synthesis Virahol as claimed in claim 6, is characterized in that described coordination agent comprises citric acid, ammonium citrate, ethylenediamine tetraacetic acid (EDTA), cetyl trimethylammonium bromide, sodium lauryl sulphate or disodium ethylene diamine tetraacetate.
CN201410433288.1A 2014-08-29 2014-08-29 Method for synthesizing isopropanol from acetic acid Pending CN104262088A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107879896A (en) * 2017-10-31 2018-04-06 山东玉皇化工有限公司 A kind of methyl acetate Hydrogenation for isopropanol method and its use catalyst preparation method

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0082641A1 (en) * 1981-12-18 1983-06-29 The Standard Oil Company Catalysts for the production of alcohols from olefins and synthesis gas and process employing such catalysts
CN102336632A (en) * 2010-07-28 2012-02-01 中国石油化工股份有限公司 Method for preparing isopropanol through gas phase hydrogenation of acetone
CN102746113A (en) * 2011-04-20 2012-10-24 中国石油化工股份有限公司 Preparation method of isopropanol
CN103657695A (en) * 2013-12-04 2014-03-26 中国科学院山西煤炭化学研究所 Catalyst for acetic acid hydrogenation synthesis of isopropyl alcohol, and preparation method and application thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0082641A1 (en) * 1981-12-18 1983-06-29 The Standard Oil Company Catalysts for the production of alcohols from olefins and synthesis gas and process employing such catalysts
CN102336632A (en) * 2010-07-28 2012-02-01 中国石油化工股份有限公司 Method for preparing isopropanol through gas phase hydrogenation of acetone
CN102746113A (en) * 2011-04-20 2012-10-24 中国石油化工股份有限公司 Preparation method of isopropanol
CN103657695A (en) * 2013-12-04 2014-03-26 中国科学院山西煤炭化学研究所 Catalyst for acetic acid hydrogenation synthesis of isopropyl alcohol, and preparation method and application thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107879896A (en) * 2017-10-31 2018-04-06 山东玉皇化工有限公司 A kind of methyl acetate Hydrogenation for isopropanol method and its use catalyst preparation method
CN107879896B (en) * 2017-10-31 2021-02-05 山东玉皇化工有限公司 Method for preparing isopropanol by methyl acetate hydrogenation

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Application publication date: 20150107