CN102041025B - Method for preparing alpha-olefin from vegetable fat - Google Patents
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- CN102041025B CN102041025B CN2009102357262A CN200910235726A CN102041025B CN 102041025 B CN102041025 B CN 102041025B CN 2009102357262 A CN2009102357262 A CN 2009102357262A CN 200910235726 A CN200910235726 A CN 200910235726A CN 102041025 B CN102041025 B CN 102041025B
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Abstract
The invention relates to a method for preparing alpha-olefin from vegetable fat. The method comprises the following steps: inputting the vegetable fat and diluted water into a tubular cracking furnace; thermally cracking under a non-catalytic condition; and separating a product after the reacting product is cooled. In the method, the renewable vegetable fat is used for preparing the alpha-olefin,so that the sources of raw materials for preparing the alpha-olefin are widened, and the C6 to C12 alpha-olefin with high value can be conveniently produced.
Description
Technical field
The present invention relates to a kind of method of producing alpha-olefin by Vegetable oil lipoprotein, specifically, is a kind of method of being produced alpha-olefin by Vegetable oil lipoprotein by the steam heat cracking.
Background technology
Linear alpha-olefin typically refers to C
4And C
4Above straight chain terminal olefine, it is the important Organic Chemicals of a class that develops rapidly over nearly 30 years, since the nineties in 20th century, ethylene oligomerization was produced the industrialization of alpha-olefin Technology, its Application Areas constantly enlarges, be widely used in comonomer, Chemicals such as synthetic lubricant base oil, tensio-active agent, softening agent, sterilant and emulsifying agent.
Along with the high speed development of world economy, alpha-olefin market still presents very fast momentum of development, and some new devices are still among building.World's alpha-olefin throughput will further be increased to more than 4,400,000 tons in 2007 from 3,700,000 tons in 2003; The demand that the demand side calendar year 2001 whole world is used for alpha-olefin is 2,500,000 tons, expects 2010 annual requirements and will be increased to 4,700,000, and average growth rate per annum is about 6.6%.Because alpha-olefin has very big market development potentiality, some main manufacturers constantly expand production capacity both at home and abroad, explore new and more cost-effective novel process, strengthen the competitiveness of product in market.
The industrialized preparing process of alpha-olefin mainly contains methods such as wax destructive distillation, ethylene oligomerization, internal olefin isomery, Fatty Alcohol(C12-C14 and C12-C18) dehydrogenation, extracting and separating, occupies an leading position with the processing method of ethylene oligomerization at present.According to statistics, there is 6% ethene in the U.S. approximately by the production of this technology for alpha-olefin.
Natural plant grease is that example is to squeeze out the palm fibre fruit (Elaeis Guineensis) from oil palm tree with the plam oil.Grease is saturated fatty, single unsaturated fatty acids, three kinds of compositions mixing of polyunsaturated fat formation, and it is mainly based on carbon, hydrogen and oxygen element, and the content of sulphur and nitrogen element seldom.Along with the progress of transgenic technology, their output is higher, is a kind of green, reproducible resource.It is used as whole food by people and surpasses the history in 5,000 years for a long time.In addition, can also be used to making the product of soap and other numerous species.
Owing to the special composition structure of Vegetable oil lipoprotein, can be considered as the raw material of oil fuel or petrochemical process.Early stage and present research mainly is to change into clean fuel and low-carbon alkene product in the Vegetable oil lipoprotein.
CN 1190471C discloses a kind of method with grease (comprising Vegetable oil lipoprotein and animal grease) biodiesel synthesis.This method is to utilize Vegetable oil lipoprotein by biological enzyme effect biodiesel synthesis, uses as clean fuel oil or blend component, is present except the purposes of above-mentioned Vegetable oil lipoprotein, the most widely used method.
US 2007/0015947A1 discloses a kind of Vegetable oil lipoprotein and has adopted two step method to produce C
2～C
5Alkene (low-carbon alkene), the first step is deviate from impurity by preprocessing means, and second step adopted conventional catalytic cracking process to produce low-carbon alkene.Because catalytic cracking process is followed the reaction mechanism of carbonium ion, its cracked product is mainly based on gasoline and diesel oil, in the splitting gas based on propylene product.
CN 1269853C (international application no PCT/JP00/00042) discloses a kind of low-carbon alpha-alkene (ethene) and has adopted oligomerisation reaction to produce catalyzer and producing and manufacturing technique that molecular weight is lower than 1000 low poly-alpha olefins, and the alpha-olefin in its product comprises C
4～C
28, carbon number range difference, purposes are also different.
It is raw material with the semi-refined wax that CN 1506442A discloses a kind of, produces C by the method for high temperature pyrolysis
5～C
13Alpha-olefin, separate this alpha-olefin by secondary steam injection technology fractionation plant again, as the raw material of synthin lubricating oil.Through overlapping reaction, normal vacuum fractionation, realized under same materials and the processing condition process goal of synchronous production 8B aircraft lube oil and No. 20 aircraft oils.
Having now and utilizing the technology of Vegetable oil lipoprotein mainly is to utilize its special structure of matter, the production biofuel, or also be a kind of selection with it as the catalytic cracking unit raw material of oil refining process, its major objective is to produce high-octane gasoline and diesel product or blend component, the catalytic cracking low-carbon alkene is mainly based on propylene product, and yield is lower.Up to the present, Vegetable oil lipoprotein is not directly reported as the technology of producing the alpha-olefin raw materials technology.
Summary of the invention
The technical problem to be solved in the present invention provides a kind of method of utilizing Vegetable oil lipoprotein to produce alpha-olefin, and this method can utilize Vegetable oil lipoprotein to produce alpha-olefin to greatest extent, and makes the reaction unit can long-term operation.
All pressure all refer to gauge pressure among the present invention.
Method provided by the invention comprises: with Vegetable oil lipoprotein and dilution water input tube cracking furnace, carry out thermo-cracking under non-catalytic condition, carry out product separation after the reaction product cooling; Reaction conditions: Vegetable oil lipoprotein is preheated to 300 ℃～450 ℃ at the convection zone of tube cracking furnace, and the temperature out of pyrolyzer is 540～680 ℃, and the pyrolyzer top hole pressure is 0.1Mpa～0.5Mpa; The residence time is 2～20s, and the weight ratio of dilution water and Vegetable oil lipoprotein is 0.01～0.2.
The main component of described Vegetable oil lipoprotein is C
12～C
24The Witepsol W-S 55 of lipid acid is preferably in plam oil, soybean oil and the rapeseed oil one or more.
The pyrolyzer temperature out is preferably 570～630 ℃.
The described residence time refers to the residence time at the tube cracking furnace radiation section.The residence time is preferably 5～15s.
The weight ratio of dilution water and Vegetable oil lipoprotein is preferably 0.05～0.15.
Among the present invention, the preheating temperature of dilution water is preferably controlled at 350 ℃～550 ℃.The preheating of dilution water can be by sharing the convection zone of tube cracking furnace or adopt independent preheating oven to realize with Vegetable oil lipoprotein; The independent preheating oven of preferred employing.
Under the preferred situation, the pyrolyzer temperature out is controlled at 540～600 ℃, and unconverted material cycle return pipe formula pyrolyzer is continued reaction, described unconverted material refers to that cleavage reaction product carries out the separation column substrate in the product separation.
Under the another kind of preferred situation, greater than 600 ℃ to 680 ℃, unconverted material does not return tube cracking furnace with the control of pyrolyzer temperature out, and described unconverted material refers to that cleavage reaction product carries out the separation column substrate in the product separation.
Described tube cracking furnace belongs to prior art, and it is made up of convection zone and radiation section two portions.
Adopt method provided by the invention, can utilize Vegetable oil lipoprotein as the thermo-cracking raw material, produce C
6～C
24Blend alpha-olefin product.
Prior art mainly is to produce alpha-olefin by wax destructive distillation and ethylene oligomerization, because reaction raw materials and reaction mechanism is different, above-mentioned technology and reaction conditions of the present invention and distribution of reaction products are all inequality.Compared with prior art, the present invention has following advantage: 1. the used raw material-Vegetable oil lipoprotein of the present invention is a kind of reproducible resource, not only enlarge the raw material sources of producing alpha-olefin, help to alleviate the contradiction of present alpha-olefin raw material supply anxiety, and long-term, the stable supply of alpha-olefin is had very important meaning; 2. method of the present invention more is conducive to produce C
6～C
24The C of mixing alpha-olefin, particularly high value
6～C
12Alpha-olefin; 3. the present invention adopts water vapor as thinner, can improve the yield of target product, and Pintsch process reaction coking is had certain restraining effect; 4. the cracking of glyceride produces a certain amount of CO and CO
2Gas can reduce the hydrocarbon partial pressure of scission reaction, improves the selectivity of scission reaction, more is conducive to the generation of alpha-olefin, reduces the scission reaction coking simultaneously.
Description of drawings
Accompanying drawing is the synoptic diagram of method provided by the present invention.
Embodiment
Below in conjunction with accompanying drawing, specifically set forth the present invention.
A kind of preferred implementation of the present invention is: Vegetable oil lipoprotein through the convection zone of tube cracking furnace, is preheated to 300 ℃～450 ℃ as the raw material of heat scission reaction.According to the requirement of operation condition, dilution water directly can be imported the convection zone of tube cracking furnace by process pipeline independently, also the preheating oven by arranging separately is preheated to 350 ℃～550 ℃ with dilution water.Reach two kinds of materials of preheating temperature after the radiation section of tube cracking furnace mixes, carry out the Pintsch process reaction, reaction conditions is: the pyrolyzer temperature out is 540～600 ℃, preferred 570～600 ℃; The pyrolyzer top hole pressure is 0.1Mpa～0.5Mpa; Reaction time: 2～20s, preferred 5～15s; The weight ratio of dilution water and Vegetable oil lipoprotein is 0.01～0.2, is preferably 0.05～0.15.Reaction product is after the cooling of quenching boiler and cracking quencher, and the alpha-olefin to different carbon numbers in normal, the vacuum fractionation tower of routine separates, and isolates the CO/CO that reaction generates at the atmospheric fractional tower cat head
2, the unreacting substance of collecting at the bottom of the fractionation Tata (wherein contain unreacted Vegetable oil lipoprotein and not the molecular substance broad in the middle of complete reaction) mixes the back to be used as the raw material of heat scission reaction with the fresh plant grease.
Second kind of preferred implementation of the present invention is: Vegetable oil lipoprotein through the convection zone of tube cracking furnace, is preheated to 300 ℃～450 ℃ as the raw material of heat scission reaction.According to the requirement of operation condition, dilution water directly can be imported the convection zone of tube cracking furnace by process pipeline independently, also the preheating oven by arranging separately is preheated to 350 ℃～550 ℃ with dilution water.Reach two kinds of materials of preheating temperature after radiation section mixes, carry out the Pintsch process reaction, reaction conditions is: the pyrolyzer temperature out is preferably greater than 600 ℃ to 630 ℃ for greater than 600 ℃ to 680 ℃; The pyrolyzer top hole pressure is 0.1Mpa～0.5Mpa; Reaction time: 2～20s, preferred 5～15s; The weight ratio of dilution water and Vegetable oil lipoprotein is 0.01～0.2, is preferably 0.05～0.15.Reaction product is after the cooling of quenching boiler and cracking quencher, and the alpha-olefin to different carbon numbers in normal, the vacuum fractionation tower of routine separates, and isolates the CO/CO that reaction generates at the atmospheric fractional tower cat head
2, the unreacting substance of collecting at the bottom of the fractionation Tata is as the charging of other oil refining complete processings.
Further specify the present invention by the following examples.Vegetable oil lipoprotein A among the embodiment is that plam oil, Vegetable oil lipoprotein B are soybean oil, and Vegetable oil lipoprotein C is rapeseed oil, and three kind of plant greases are commercially available tank oil.
Embodiment 1
With a kind of Vegetable oil lipoprotein A, its character sees Table 1, distinguish separately as the charging of simulation steam heat cracking performance evaluation experimental device with dilution water, simulation cracking evaluation experimental device is made up of feed system, raw material preheating, scission reaction system, quenching system and product separation system five parts, and complete assembly is by a computer-controlled operation and monitoring operation.The thermal cracking products that generates carries out product and separates with 360 ℃ according to 200 ℃ of cut points respectively, and＞360 ℃ cut is as unconverted material.The main operational condition of technological process that thermo-cracking is produced alpha-olefin is: 320 ℃ of Vegetable oil lipoprotein preheating temperatures, the control of water preheat temperature are in 320 ℃ (sharing preheating sections), heat scission reaction temperature: the weight ratio of 560 ℃, pyrolyzer top hole pressure: 0.15Mpa (gauge pressure), reaction time: 12.7s, dilution water and Vegetable oil lipoprotein is 0.03, and the cracking evaluation test the results are shown in Table 2.
Embodiment 2
Adopt testing apparatus and test method and the step identical with embodiment 1, with a kind of Vegetable oil lipoprotein A, its character sees Table 1, distinguish separately as the charging of simulation thermo-cracking benchmark test device with dilution water, the main operational condition of technological process that thermo-cracking is produced alpha-olefin is: 380 ℃ of Vegetable oil lipoprotein preheating temperatures, the control of water preheat temperature is 380 ℃ (sharing preheating section), heat scission reaction temperature: 600 ℃, pyrolyzer top hole pressure: 0.30Mpa (gauge pressure), reaction time: 7.6s, the weight ratio of dilution water and Vegetable oil lipoprotein is 0.09, and the cracking evaluation test the results are shown in Table 2.
Embodiment 3
Adopt testing apparatus and test method and the step identical with embodiment 1, with a kind of Vegetable oil lipoprotein A, its character sees Table 1, distinguish separately as the charging of simulation thermo-cracking benchmark test device with dilution water, the main operational condition of technological process that thermo-cracking is produced alpha-olefin is: 450 ℃ of Vegetable oil lipoprotein preheating temperatures, the control of water preheat temperature is 450 ℃ (sharing preheating section), heat scission reaction temperature: 650 ℃, pyrolyzer top hole pressure: 0.50Mpa (gauge pressure), reaction time: 2.9s, the weight ratio of dilution water and Vegetable oil lipoprotein is 0.15, and the cracking evaluation test the results are shown in Table 2.
Data show in the table 2: Vegetable oil lipoprotein A carries out the steam heat cracking, under selected scission reaction severity condition, all can generate the mixing alpha-olefin of higher proportion among embodiment 1, embodiment 2 and the embodiment 3, no matter be that alpha-olefin yield in light constituent (＜200 ℃ of cuts) or the heavy constituent (200 ℃～360 ℃ cuts) all exists maximum value, the more high unconverted material yield of thermo-cracking severity is more low, need the amount of circulation more little, but can be affected in the operational cycle.
Embodiment 4
Adopt testing apparatus and test method and the step identical with embodiment 1, with a kind of Vegetable oil lipoprotein B, its character sees Table 1, distinguish separately as the charging of simulation thermo-cracking benchmark test device with dilution water, the main operational condition of technological process that thermo-cracking is produced alpha-olefin is: 450 ℃ of Vegetable oil lipoprotein preheating temperatures, the control of water preheat temperature is at 500 ℃ (independent preheating sections), heat scission reaction temperature: 610 ℃, pyrolyzer top hole pressure: 0.20Mpa (gauge pressure), reaction time: 6.7s, the weight ratio of dilution water and Vegetable oil lipoprotein is 0.10, and the cracking evaluation test the results are shown in Table 3.
Comparative Examples 1
Adopt testing apparatus and test method and the step identical with embodiment 1, reaction process is not added dilution water.With a kind of Vegetable oil lipoprotein B, its character sees Table 1, separately as the charging of simulation thermo-cracking benchmark test device, the main operational condition of technological process that thermo-cracking is produced alpha-olefin is: 450 ℃ of Vegetable oil lipoprotein preheating temperatures, heat scission reaction temperature: 610 ℃, pyrolyzer top hole pressure: 0.20Mpa (gauge pressure), reaction time: 6.7s, the cracking evaluation test the results are shown in Table 3.
Embodiment 5
Adopt testing apparatus and test method and the step identical with embodiment 1, with a kind of Vegetable oil lipoprotein C, its character sees Table 1, distinguish separately as the charging of simulation thermo-cracking benchmark test device with dilution water, the main operational condition of technological process that thermo-cracking is produced alpha-olefin is: 400 ℃ of Vegetable oil lipoprotein preheating temperatures, the control of water preheat temperature is at 450 ℃ (independent preheating sections), heat scission reaction temperature: 630 ℃, pyrolyzer top hole pressure: 0.20Mpa (gauge pressure), reaction time: 7.6s, the weight ratio of dilution water and Vegetable oil lipoprotein is 0.10, and the cracking evaluation test the results are shown in Table 4.
Comparative Examples 2
Adopt testing apparatus and test method and the step identical with embodiment 1, reaction process is not added dilution water.With a kind of Vegetable oil lipoprotein C, its character sees Table 1, separately as the charging of simulation thermo-cracking benchmark test device, the main operational condition of technological process that thermo-cracking is produced alpha-olefin is: 400 ℃ of Vegetable oil lipoprotein preheating temperatures, heat scission reaction temperature: 630 ℃, pyrolyzer top hole pressure: 0.20Mpa (gauge pressure), reaction time: 7.6s, the cracking evaluation test the results are shown in Table 4.
Two kinds of different Vegetable oil lipoprotein cracking evaluating datas of analytical table 3 and table 4, compare as can be known with the data of table 2 simultaneously: different feedstock properties and structure are formed, thermo-cracking is generated the content difference of the favourable active principle of target alpha-olefin product, also there are larger difference in cracking alpha-olefin product yield and distribution, select Vegetable oil lipoprotein to make the raw material of preparing alpha-olefine by thermal cracking, should select the higher relatively Vegetable oil lipoprotein of saturated fatty acid content; Adopt suitable operational conditions such as scission reaction temperature, can improve the cracking yield of alpha-olefin product.Embodiment 4 and Comparative Examples 1, embodiment 5 compare as can be known with the data of Comparative Examples 2, after adding dilution water, blend alpha-olefin product the yield of the different fractions section that scission reaction generates is than all increasing under the condition of not adding dilution water, the coking yield of scission reaction process is low, and unconverted material yield is low.
Embodiment 6
Adopt testing apparatus and test method and the step identical with embodiment 1, adopt embodiment 1 reacted unconverted material and a kind of Vegetable oil lipoprotein A simultaneously, by after 12.45: 87.55 the mixed, as the charging of simulation steam heat cracking performance evaluation experimental device, the main operational condition of technological process that thermo-cracking is produced alpha-olefin is identical with embodiment 1, and the cracking evaluation test the results are shown in Table 5.
Embodiment 7
Adopt testing apparatus and test method and the step identical with embodiment 1, adopt embodiment 3 reacted unconverted materials and a kind of Vegetable oil lipoprotein A simultaneously, by after 3.62: 96.38 the mixed, as the charging of simulation steam heat cracking performance evaluation experimental device, the main operational condition of technological process that thermo-cracking is produced alpha-olefin is identical with embodiment 3, and the cracking evaluation test the results are shown in Table 5.
Analytical table 2 and table 5 Vegetable oil lipoprotein A and Vegetable oil lipoprotein A are with after unconverted material mixes, adopt respectively under identical cracking severity condition steam heat cracking evaluating data as can be known, when adopting the cracking operation condition (embodiment 1 and embodiment 6) that relatively relaxes, the product yield data of unconverted material cycle cracking are suitable with pure Vegetable oil lipoprotein A thermo-cracking alpha-olefin yield.When adopting relatively harsh cracking operation condition (embodiment 3 and embodiment 7), unconverted material yield is also lower, product yield data and the pure Vegetable oil lipoprotein A thermo-cracking alpha-olefin yield of circulation back cracking have certain gap, can consider under this condition unconverted material is delivered to other oil refining complete processing devices, make rational use of resources to greatest extent.
Table 1
Table 2
Table 3
Table 4
Table 5
Claims (9)
1. a method of producing alpha-olefin by Vegetable oil lipoprotein comprises: with Vegetable oil lipoprotein and dilution water input tube cracking furnace, carry out thermo-cracking under non-catalytic condition, carry out product separation after the reaction product cooling; Reaction conditions: Vegetable oil lipoprotein is preheated to 300 ℃～450 ℃ at the convection zone of tube cracking furnace, and the temperature out of pyrolyzer is 540～680 ℃, and the pyrolyzer top hole pressure is 0.1Mpa～0.5Mpa; The residence time is 2～20s, and the weight ratio of dilution water and Vegetable oil lipoprotein is 0.01～0.2; The main component of described Vegetable oil lipoprotein is C
12～C
24The Witepsol W-S 55 of lipid acid.
2. in accordance with the method for claim 1, it is characterized in that described Vegetable oil lipoprotein is one or more in plam oil, soybean oil and the rapeseed oil.
3. in accordance with the method for claim 1, it is characterized in that the pyrolyzer temperature out is 570～630 ℃.
4. in accordance with the method for claim 1, it is characterized in that the residence time is 5～15s.
5. in accordance with the method for claim 1, it is characterized in that the weight ratio of dilution water and Vegetable oil lipoprotein is 0.05～0.15.
6. in accordance with the method for claim 1, it is characterized in that the preheating temperature of dilution water is 350 ℃～550 ℃.
7. according to claim 1 or 6 described methods, it is characterized in that, by sharing the convection zone of tube cracking furnace or adopt independent preheating oven preheating dilution water with Vegetable oil lipoprotein.
8. in accordance with the method for claim 1, it is characterized in that, the pyrolyzer temperature out is controlled at 540～600 ℃, and unconverted material cycle return pipe formula pyrolyzer is continued reaction.
9. in accordance with the method for claim 1, it is characterized in that greater than 600 ℃ to 680 ℃, unconverted material does not return tube cracking furnace with pyrolyzer temperature out control.
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| CN113930279A (en) * | 2021-11-02 | 2022-01-14 | 邦仕顿润滑科技股份有限公司 | Biodegradable plant-based anti-wear lubricating oil and preparation method thereof |
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|---|---|---|---|---|
| CN1080944A (en) * | 1992-06-22 | 1994-01-19 | 化学工业部北京化工研究院 | Process for preparing alpha-olefine by thermal cracking of paraffin wax |
| CN101092318A (en) * | 2006-06-21 | 2007-12-26 | 中国科学院大连化学物理研究所 | Method for producing olefin by using vegetable fat and animal fat |
| CN101213159A (en) * | 2005-07-06 | 2008-07-02 | 英尼奥斯欧洲有限公司 | Process for the production of linear alpha-olefins |
-
2009
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1080944A (en) * | 1992-06-22 | 1994-01-19 | 化学工业部北京化工研究院 | Process for preparing alpha-olefine by thermal cracking of paraffin wax |
| CN101213159A (en) * | 2005-07-06 | 2008-07-02 | 英尼奥斯欧洲有限公司 | Process for the production of linear alpha-olefins |
| CN101092318A (en) * | 2006-06-21 | 2007-12-26 | 中国科学院大连化学物理研究所 | Method for producing olefin by using vegetable fat and animal fat |
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