CN102659724B - A kind of preparation method of succinyl oxide - Google Patents
A kind of preparation method of succinyl oxide Download PDFInfo
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- CN102659724B CN102659724B CN201210107128.9A CN201210107128A CN102659724B CN 102659724 B CN102659724 B CN 102659724B CN 201210107128 A CN201210107128 A CN 201210107128A CN 102659724 B CN102659724 B CN 102659724B
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Abstract
The invention discloses a kind of preparation method of succinyl oxide.Comprise the steps: under hydrogenation catalyst existent condition, MALEIC ANHYDRIDE and hydrogen react through liquid-phase hydrogenatin and obtain described succinyl oxide; Described hydrogenation catalyst comprises carrier and is carried on the active ingredient on this carrier, described active ingredient is selected from one or more elements in IB race in the periodic table of chemical element, IIB race, group vib, VIIB and group VIIIB, and described carrier is selected from oxide compound and the gac of one or more elements in IA race in the periodic table of chemical element, IIA race, IIIA race, IVA race, VA and IVB race.The invention provides that the synthesis of a kind of hydrogenation catalyst is simple, reaction conditions is gentle, process is continuous and high yield prepares the method for succinyl oxide.
Description
Technical field
The present invention relates to a kind of preparation method of succinyl oxide.
Background technology
Pharmaceutically, succinyl oxide can be used for producing sulfa drug, vitamin A, vitamins B
6, hemostatic drug and diuretic(s) etc., with erythromycin effect synthetic antibacterial drug; Agriculturally, succinyl oxide and the obtained N dimethylamine base succinic diamide of unsymmetrical dimethyl hydrazine reaction, be a kind of low toxicity, efficiently plant growth inhibitor, regulate nutrient, increase drought resisting, disease-resistant, freezing tolerance, widespread use in the cash crop such as fruit and vegetable.In addition, succinyl oxide can also be used for food to be added, and the wherein food processing aid that specifies of GB2760-90, the synthesis of medicine, agricultural chemicals, ester class and resin, also can be used for the synthesis and analysis reagent of succinic acid.Market most with prospects, namely as the main raw material of biodegradable plastic poly butylene succinate (PBS).
Current production succinyl oxide mainly contains three kinds of technological lines: i.e. succsinic acid evaporation, biological fermentation process and maleic anhydride hydrogenation method.Succsinic acid evaporation first prepares succsinic acid, then succsinic acid dehydration is obtained succinyl oxide (abbreviation two step method).The method for making of succinic acid is that paraffin oxidation obtains mixed dibasic acid oxidized petroleum waves, through overheated steam distillation, removes unstable hydroxyl oil-soluble acid and ester, and aqueous phase succinic acid, through dehydration, is dried, obtained succinic acid; Two step method produces that Succinic anhydried ubiquity operational path is long, operation is many, equipment and the shortcoming such as initial cost is high, product cost is high, quality is unstable.Biological fermentation process technological line, there is production cycle length, complex procedures, fermentation waste water is many, be difficult to the shortcoming of industrial mass production in the productive rate about 85% of its succinic acid.Maleic anhydride hydrogenation method is divided into electrochemical reducing and the direct shortening method of cis-butenedioic anhydride, and electrochemical reducing is produced succinyl oxide and had current consumption greatly, the shortcomings such as ionic membrane cracky, anode consumption are serious.Therefore the direct shortening method of cis-butenedioic anhydride is the good method of producing succinyl oxide at present.For this reason, exploitation cis-butenedioic anhydride direct hydrogenation produces raw catalyst and the technique of Succinic anhydried, decreases flow process, reduces energy consumption.
Chinese patent application CN1078716A has set forth following method: at 160 ~ 210 DEG C, hydrogen dividing potential drop is 1.2 ~ 2.0MPa, reaction times is 30 ~ 120min, catalyst quality mark is 4% ~ 10%, using nickel system metal as hydrogenation catalyst, under batch reactor condition, do not use solvent materials direct heating to molten state, carry out the direct catalytic hydrogenation of cis-butenedioic anhydride, conversion rate of maleic anhydride is greater than 99%, succinyl oxide yield about 90%.Chinese patent application CN101805318A discloses following method: in forerunner's alloy powder nickel, aluminium, with the addition of the third component, as Fe, the mixture of one or more in Mn, Sn, Mo and Cr, under adopting quenching Raney nickel mild conditions, carry out cis-butenedioic anhydride shortening and prepare succinyl oxide; This catalyzer carries out partially modified to traditional skeleton nickel, in catalyzer use procedure, need to utilize caustic soda to carry out dissolution of metals aluminium, produces more waste lye and a large amount of hydrogen of release.Chinese patent application CN1453066A discloses at catalyst n i/SiO
2-Al
2o
3under effect, use nickelous nitrate, tetraethoxy or tetraethoxy and aluminum nitrate, ethanol, generate gel by the pH value of acetic acid, ammoniacal liquor or urea regulator solution; Roasting 400-550 DEG C, reduces under 400-580 DEG C of preparation condition, carries out maleic anhydride hydrogenation and prepare succinyl oxide test in reactor.SiO is prepared owing to using teos hydrolysis
2carrier, significantly increases Catalyst Production cost.US5616730 reports, under skeleton nickel or platinum group catalyst, 120-150 DEG C, hydrogen 1-15MPa condition, carries out the reaction of cis-butenedioic anhydride liquid phase catalytic hydrogenation and prepares succinyl oxide.In a word, above-mentioned reaction process, in batch reactor, is carried out maleic anhydride hydrogenation and is prepared succinyl oxide, obviously there is the shortcomings such as throughput is little, powder dress catalyzer and product separation difficulty, labor strength is large, environmental pollution is larger.
U.S. Patent application US5770744, under VIIIB catalyzer, 60-180 DEG C, hydrogen 10-30MPa condition, fixed bed carries out the reaction of cis-butenedioic anhydride liquid phase catalytic hydrogenation continuously and prepares succinyl oxide; This reaction process pressure is higher, increases device fabrication difficulty.In addition, Chinese patent CN101502802A, at active component nickel content 13-20%, promotor 1-7%, loaded catalyst, carrier is SiO
2, Al
2o
3or SiO
2-Al
2o
3under complex body and fixed bed condition, carry out cis-butenedioic anhydride continuous hydrogenation and prepare Succinic anhydried, succinyl oxide reaches the yield of about 98.8%.But its deficiency is carrier to be needed 400-800 DEG C of calcination process, adds Kaolinite Preparation of Catalyst difficulty; After catalyst reduction simultaneously, need through oxygen Passivation Treatment or protect in a liquid, adding catalyzer and use difficulty and security.
Summary of the invention
The object of this invention is to provide a kind of preparation method of succinyl oxide.
The preparation method of a kind of succinyl oxide provided by the invention, comprises the steps: under hydrogenation catalyst existent condition, and MALEIC ANHYDRIDE and hydrogen react through liquid-phase hydrogenatin and obtains described succinyl oxide;
Described hydrogenation catalyst comprises carrier and is carried on the active ingredient on this carrier, described active ingredient is selected from one or more elements in IB race in the periodic table of chemical element, IIB race, group vib, VIIB and group VIIIB, and described carrier is selected from oxide compound and the gac of one or more elements in IA race in the periodic table of chemical element, IIA race, IIIA race, IVA race, VA and IVB race.
In above-mentioned preparation method, in described hydrogenation catalyst, the mass percentage of described active ingredient can be 0.1% ~ 85%.
In above-mentioned preparation method, in described hydrogenation catalyst, described active ingredient specifically can be at least one in nickel, palladium, cobalt, rhenium, rhodium, iridium and platinum; Described carrier specifically can be at least one in gac, aluminum oxide, zinc oxide, chromic oxide, silicon oxide, zirconium white and titanium oxide.
In above-mentioned preparation method, described hydrogenation catalyst can be sedimentation type catalyzer or immersion type carried catalyst.Sedimentation type catalyzer can be prepared as follows: first by described active ingredient from their salts solution, especially from the solution of their nitrate and/or acetate, by adding basic metal and/or alkaline earth metal hydroxides solution and/or carbonate solution, such as the oxyhydroxide of indissoluble, oxide hydrate, basic salt or carbonate deposition are out, the throw out obtained filters subsequently, washing and drying, and calcine, usually at 250 ~ 700 DEG C, especially corresponding oxide compound is transferred to 300 ~ 500 DEG C of calcinings, the oxide compound of mixed oxide and/or mixed valence, they pass through with hydrogen or hydrogeneous gas, usually at 50 ~ 700 DEG C, especially 100 ~ 400 DEG C process, be reduced into corresponding metal and/or the oxide compound compared with suboxide valency, and change into the form of their real catalytic activity, other suitable reductive agent can be selected for this reason, as: formaldehyde, hydrazine, to replace hydrogen, have economic worth or hydrogen most certainly, usually under certain reductive condition, be reacted to and do not consume hydrogen, or the generation water yield does not become principle.Prepared by supported catalyst: can adopt active ingredient described in described carrier direct impregnation, or described active ingredient is precipitated out then advantageously to carrier simultaneously from relevant salts solution.
In above-mentioned preparation method, described hydrogenation catalyst can by described carrier, be carried on active ingredient on this carrier and auxiliary agent forms; Described auxiliary agent can be selected from least one in copper, barium, potassium, palladium and tin, and the mass percentage of described auxiliary agent can be 0.05% ~ 2.5%, specifically can be 0.08% or 0.1%.
In above-mentioned preparation method, described hydrogenation catalyst is nickel-base hydrogenation catalyst, and described nickel-base hydrogenation catalyst is nickel/palladium/gac hydrogenation catalyst, nickel/aluminum oxide hydrogenation catalyst, palladium/nickel/aluminum oxide hydrogenation catalyst, copper/nickel/aluminum oxide hydrogenation catalyst, copper/nickel/aluminium oxide-titanium oxide hydrogenation catalyst, copper/nickel/aluminium oxide-zirconium oxide hydrogenation catalyst or copper/nickel/alumina-silica zinc hydrogenation catalyst.
In above-mentioned preparation method, in described nickel-base hydrogenation catalyst, the content of nickel is in nickel oxide, and the mass percentage of nickel oxide can be 12% ~ 40%, specifically can be 15%, 18%, 20% or 25%.
In above-mentioned preparation method, the temperature of described liquid-phase hydrogenatin reaction can be 80 ~ 160 DEG C, specifically can be 85 DEG C, 90 DEG C, 95 DEG C, 130 DEG C, 140 DEG C, 148 DEG C, 150 DEG C or 155 DEG C, pressure can be 2.5 ~ 4MPa, specifically can be 2.5MPa, 3MPa, 3.2MPa or 3.5MPa.
In above-mentioned preparation method, the liquid air speed of described liquid-phase hydrogenatin reaction can be 0.05hr
-1~ 0.3hr
-1, specifically can be 0.1hr
-1, 0.13hr
-1, 0.15hr
-1, 0.2hr
-1or 0.25hr
-1, hydrogen can be (10 ~ 80) with the molfraction ratio of MALEIC ANHYDRIDE: 1, specifically can be 20: 1,40: 1,60: 1,65: 1,70: 1 or 80: 1.
In above-mentioned preparation method, described liquid-phase hydrogenatin reaction can be carried out in fixed-bed reactor or paste state bed reactor; From the crude product of described fixed-bed reactor or paste state bed reactor out heat, through being cooled to thick product, getting final product sampling analysis, obtaining its crude product and forming, grasping the activity and selectivity of catalyzed reaction.Crude product can process by traditional mode, and by fractional distillation, removing by product, obtains qualified product.
The invention provides that the synthesis of a kind of hydrogenation catalyst is simple, reaction conditions is gentle, process is continuous and high yield prepares the method for succinyl oxide.
Embodiment
The experimental technique used in following embodiment if no special instructions, is ordinary method.
Material used in following embodiment, reagent etc., if no special instructions, all can obtain from commercial channels.
In the following embodiments, the transformation efficiency of cis-butenedioic anhydride and the selectivity of succinyl oxide are all measured by gas-chromatography hydrogen flame detector, concrete measuring method is: adopt capillary column 30m × 320um × 0.5um, DB-Waxetr, post case condition, initial temperature 30 DEG C stops 9 minutes, is raised to 140 DEG C and stops 4 minutes, then be raised to 250 DEG C with 10 DEG C/min with 10 DEG C/min; Detector 260 DEG C, sample size 0.2ul.
Transformation efficiency=100% of cis-butenedioic anhydride × (there occurs the cis-butenedioic anhydride amount of the cis-butenedioic anhydride amount of reaction/initial);
The total amount that cis-butenedioic anhydride amount/cis-butenedioic anhydride that the selectivity of succinyl oxide=be converted into object product succinyl oxide consumes transforms.
Embodiment 1, prepare succinyl oxide
In the fixed-bed reactor (Φ 14 × 1000mm) that has indirect heating, flow control, load 20 ~ 40 object 15g nickel-palladium/activated-carbon catalysts (NiO content 15%, Pd content 0.08%, gac 84.92%); Method for making: take required nickelous nitrate and palladium nitrate solution, mix with gac, then uses ammonia soln neutralization precipitation, throw out after filtration, washing and dry, calcining at 480 DEG C under a nitrogen, last fragmentation is sieved and is shapingly namely obtained nickel-palladium/activated-carbon catalyst.
At 2.5MPa, liquid air speed 0.25hr
-1with under hydrogen acid anhydride mol ratio 20: 1 condition, when temperature of reaction 85 DEG C, conversion rate of maleic anhydride 92.5%, succinyl oxide selectivity 99.5%; When temperature of reaction 130 DEG C, cis-butenedioic anhydride (MALEIC ANHYDRIDE) transformation efficiency 98.7%, succinyl oxide selectivity 99.1%; When temperature of reaction 150 DEG C, conversion rate of maleic anhydride 100%, succinyl oxide selectivity 98.5%.
Embodiment 2, prepare succinyl oxide
By the method that embodiment 1 is same, in fixed-bed reactor, load 15g20 ~ 40 object nickel/aluminium oxide catalyst (NiO content 20%, γ-Al
2o
380%); Preparation method: nickelous nitrate first carries out acidity allotment with ammoniacal liquor, then required γ-Al
2o
3carrier is poured into, and the carrier after dipping is 110 DEG C of dryings, and 450 DEG C of roastings, last fragmentation is sieved shaping.
At 3.5MPa, liquid air speed 0.2hr
-1with under hydrogen acid anhydride mol ratio 40: 1 condition, when temperature of reaction 90 DEG C, conversion rate of maleic anhydride 85.5%, succinyl oxide selectivity 99.6%; During temperature of reaction 140 DEG C, conversion rate of maleic anhydride 100%, succinyl oxide selectivity 98.8%.
Embodiment 3, prepare succinyl oxide
By the method that embodiment 1 is same, in fixed-bed reactor, load 15g20 ~ 40 object nickel-palladium/aluminium oxide catalyst (NiO18%, Pd0.1%, γ-Al
2o
381.9%); Preparation method: nickelous nitrate and Palladous nitrate first carry out acidity allotment with ammoniacal liquor, then required γ-Al
2o
3carrier is poured into, and the carrier after dipping is 110 DEG C of dryings, and 450 DEG C of roastings, last fragmentation is sieved shaping.
At 3MPa, liquid air speed 0.13hr
-1with under hydrogen acid anhydride mol ratio 80: 1 condition, when temperature of reaction 95 DEG C, conversion rate of maleic anhydride 90.6%, succinyl oxide selectivity 99.7%; During temperature of reaction 150 DEG C, conversion rate of maleic anhydride 100%, succinyl oxide selectivity 99.1%.
Embodiment 4, prepare succinyl oxide
By the method that embodiment 1 is same, in fixed-bed reactor, load 15g20 ~ 40 object nickel-copper/aluminium oxide catalyst (NiO25%, CuO1.5%, γ-Al
2o
373.5%); Preparation method: nickelous nitrate and cupric nitrate first carry out acidity allotment with ammoniacal liquor, then required γ-Al
2o
3carrier is poured into, and the carrier after dipping is 110 DEG C of dryings, and 450 DEG C of roastings, last fragmentation is sieved shaping.
At 3MPa, liquid air speed 0.13hr
-1with under hydrogen acid anhydride mol ratio 60: 1 condition, when temperature of reaction 95 DEG C, conversion rate of maleic anhydride 88.4%, succinyl oxide selectivity 99.3%; During temperature of reaction 155 DEG C, conversion rate of maleic anhydride 100%, succinyl oxide selectivity 98.9%.
Embodiment 5, prepare succinyl oxide
By the method that embodiment 1 is same, in fixed-bed reactor, load 15g20 ~ 40 object nickel-copper/alumina-silica titanium catalyst (NiO18%, CuO1.5%, γ-Al
2o
360.5%, TiO
220%); Preparation method: titanium and the aluminum salt solution of first proportionally preparing solubility, carry out in acidity with ammoniacal liquor and form gel precipitation, throw out after filtration, washing, dry, 500 DEG C of calcinings, fragmentation is sieved preparation 20 ~ 40 order composite alumina-titanium dioxide carrier, then nickelous nitrate and cupric nitrate is first carried out acidity allotment with ammoniacal liquor, required aluminum oxide-titanium dioxide carrier is poured into, carrier after dipping 110 DEG C of dryings, 450 DEG C of roastings.
At 3.5MPa, liquid air speed 0.15hr
-1with under hydrogen acid anhydride mol ratio 70: 1, when temperature of reaction 90 DEG C, conversion rate of maleic anhydride 90.5%, succinyl oxide selectivity 99.5%; During temperature of reaction 150 DEG C, conversion rate of maleic anhydride 100%, succinyl oxide selectivity 98.7%.
Embodiment 6, prepare succinyl oxide
By the method that embodiment 1 is same, in fixed-bed reactor, load 15g20 ~ 40 object nickel-copper/alumina-silica Zr catalyst (NiO18%, CuO1.5%, γ-Al
2o
365.5%, ZrO
215%); Preparation method: zirconium and the aluminum salt solution of first proportionally preparing solubility, to carry out in acidity with ammoniacal liquor and forms gel precipitation, throw out after filtration, washing, dry, 500 DEG C of calcinings, fragmentation is sieved preparation 20 ~ 40 order composite alumina-Zirconia carrier; Then nickelous nitrate and cupric nitrate are first carried out acidity allotment with ammoniacal liquor, required alumina-zirconia carriers are poured into, the carrier after dipping 110 DEG C of dryings, 450 DEG C of roastings.
At 3.2MPa, liquid air speed 0.15hr
-1with under hydrogen acid anhydride mol ratio 65: 1 condition, when temperature of reaction 86 DEG C, conversion rate of maleic anhydride 88.5%, succinyl oxide selectivity 99.7%; During temperature of reaction 140 DEG C, conversion rate of maleic anhydride 100%, succinyl oxide selectivity 99.2%.
Embodiment 7, prepare succinyl oxide
By the method that embodiment 1 is same, in fixed-bed reactor, load 15g20 ~ 40 object nickel-copper/alumina-silica zinc catalyst (NiO18%, CuO1.5%, γ-Al
2o
370.5%, ZnO10%); Preparation method: zinc and the aluminum salt solution of first proportionally preparing solubility, carries out neutralization with sodium carbonate and forms precipitation, throw out after filtration, washing, dry, 480 DEG C of calcinings, shaping fragmentation is sieved preparation 20 ~ 40 order composite alumina-Zirconia carrier; Then nickelous nitrate and cupric nitrate are first carried out acidity allotment with ammoniacal liquor, required aluminum oxide-zinc oxide carrier are poured into, the carrier after dipping 110 DEG C of dryings, 450 DEG C of roastings.
At 3.5MPa, liquid air speed 0.1hr
-1with under hydrogen acid anhydride mol ratio 50: 1 condition, when temperature of reaction 95 DEG C, conversion rate of maleic anhydride 91.5%, succinyl oxide selectivity 99.1%; During temperature of reaction 148 DEG C, conversion rate of maleic anhydride 100%, succinyl oxide selectivity 98.3%.
Claims (4)
1. a preparation method for succinyl oxide, comprises the steps: under hydrogenation catalyst existent condition, and MALEIC ANHYDRIDE and hydrogen react through liquid-phase hydrogenatin and obtains described succinyl oxide;
Described hydrogenation catalyst comprises carrier and is carried on the active ingredient on this carrier,
Described active ingredient is nickel; Described carrier is at least one in gac, aluminum oxide, zinc oxide, zirconium white and titanium oxide;
Described hydrogenation catalyst is nickel-base hydrogenation catalyst, and in described nickel-base hydrogenation catalyst, the content of nickel is in nickel oxide, and the mass percentage of nickel oxide is 15% ~ 25%;
The preparation method of described hydrogenation catalyst is as follows: adopt active ingredient described in described carrier direct impregnation or described active ingredient is precipitated out to described carrier simultaneously from relevant salts solution;
The temperature of described liquid-phase hydrogenatin reaction is 130 ~ 155 DEG C, and pressure is 2.5 ~ 4MPa;
The liquid air speed of described liquid-phase hydrogenatin reaction is 0.05hr
-1~ 0.3hr
-1, hydrogen is (10 ~ 80) with the molfraction ratio of MALEIC ANHYDRIDE: 1.
2. method according to claim 1, is characterized in that: described hydrogenation catalyst by described carrier, be carried on active ingredient on this carrier and auxiliary agent forms; Described auxiliary agent is selected from least one in copper, barium, potassium, palladium and tin, and the mass percentage of described auxiliary agent is 0.05% ~ 2.5%.
3. method according to claim 1, is characterized in that: described nickel-base hydrogenation catalyst is nickel/palladium/gac hydrogenation catalyst, nickel/aluminum oxide hydrogenation catalyst, palladium/nickel/aluminum oxide hydrogenation catalyst, copper/nickel/aluminum oxide hydrogenation catalyst, copper/nickel/aluminium oxide-titanium oxide hydrogenation catalyst, copper/nickel/aluminium oxide-zirconium oxide hydrogenation catalyst or copper/nickel/alumina-silica zinc hydrogenation catalyst.
4. method according to claim 1, is characterized in that: described liquid-phase hydrogenatin reaction is carried out in fixed-bed reactor or paste state bed reactor.
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Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103769117B (en) * | 2012-10-24 | 2015-11-18 | 中国石油化工股份有限公司 | A kind of maleic anhydride hydrogenation prepares succinic anhydride Catalysts and its preparation method and application |
| CN103769105B (en) * | 2012-10-24 | 2016-01-06 | 中国石油化工股份有限公司 | A kind of maleic anhydride hydrogenation prepares Catalysts and its preparation method and the application of succinic anhydride |
| CN103007929B (en) * | 2012-12-07 | 2018-01-12 | 上海华谊（集团）公司 | The Pd bases catalyst of colloidal deposition method preparation, preparation method and application |
| CN104368358B (en) * | 2014-10-11 | 2017-06-06 | 中国科学院青岛生物能源与过程研究所 | It is a kind of suitable for the catalyst of butanedioic acid hydrogenation reaction and its preparation and process for selective hydrogenation |
| CN104399469A (en) * | 2014-12-05 | 2015-03-11 | 复旦大学 | Catalyst for catalyzing maleic anhydride and hydrogenating to prepare butanedioic anhydride under low temperature and low pressure and preparation method of catalyst |
| CN105833863A (en) * | 2015-01-13 | 2016-08-10 | 广东工业大学 | Catalyst for preparing succinic anhydride from maleic anhydride through low-temperature hydrogenation and preparation method and application of catalyst |
| CN104874416B (en) * | 2015-05-13 | 2017-08-25 | 山西大学 | A kind of maleic anhydride hydrogenation prepares succinic anhydride catalyst and preparation method thereof |
| CN106861702A (en) * | 2017-02-28 | 2017-06-20 | 山西大学 | It is a kind of that the catalyst and its preparation method and application for being directly synthesized succinic acid are mutually hydrogenated with for cis-butenedioic anhydride water |
| CN108709948A (en) * | 2018-04-27 | 2018-10-26 | 河南能源化工集团鹤壁煤化工有限公司 | A method of quickly measuring industrial succinic anhydride purity using gas chromatography |
| CN110227488A (en) * | 2019-06-25 | 2019-09-13 | 河南能源化工集团研究总院有限公司 | A kind of maleic anhydride hydrogenation prepares catalyst of succinic anhydride and preparation method thereof |
| CN112661625B (en) * | 2021-03-16 | 2021-06-22 | 中化学科学技术研究有限公司 | Preparation process of succinic acid |
| CN113735805A (en) * | 2021-07-06 | 2021-12-03 | 上海昶法新材料有限公司 | Process for preparing alkenyl succinic anhydride |
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| CN101502802A (en) * | 2009-03-18 | 2009-08-12 | 山西大学 | Catalyst for continuous production of succinic anhydride from hydrogenation of maleic anhydride and preparation method thereof |
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Address after: 101407 No.1, south 2nd Yueyuan street, C District, Yanqi Development Zone, Huairou District, Beijing Patentee after: Zhongke synthetic oil Technology Co.,Ltd. Address before: 101407 No.1, south 2nd Yueyuan street, C District, Yanqi Development Zone, Huairou District, Beijing Patentee before: SYNFUELS CHINA TECHNOLOGY Co.,Ltd. |
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