EP1390329B1 - Verfahren zur herstellung eines mikrokristallinen paraffins - Google Patents

Verfahren zur herstellung eines mikrokristallinen paraffins Download PDF

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Publication number
EP1390329B1
EP1390329B1 EP02732741.0A EP02732741A EP1390329B1 EP 1390329 B1 EP1390329 B1 EP 1390329B1 EP 02732741 A EP02732741 A EP 02732741A EP 1390329 B1 EP1390329 B1 EP 1390329B1
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EP
European Patent Office
Prior art keywords
paraffin
catalyst
paraffins
microcrystalline
process according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP02732741.0A
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German (de)
English (en)
French (fr)
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EP1390329A2 (de
Inventor
Michael Matthäi
Günter Hildebrand
Helmuth Schulze-Trautmann
Thorsten Butz
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Hywax GmbH
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Sasol Wax GmbH
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Publication date
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Publication of EP1390329A2 publication Critical patent/EP1390329A2/de
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • C10G45/58—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins
    • C10G45/60—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins characterised by the catalyst used
    • C10G45/64—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins characterised by the catalyst used containing crystalline alumino-silicates, e.g. molecular sieves
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1022—Fischer-Tropsch products
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S208/00—Mineral oils: processes and products
    • Y10S208/95—Processing of "fischer-tropsch" crude

Definitions

  • the invention relates to a method for producing a microcrystalline paraffin.
  • microcrystalline paraffin also known as microwaxes
  • n-alkanes branched isoalkanes and alkyl-substituted cycloalkanes (naphthenes) as well as - albeit usually small - proportions of aromatics.
  • the content of iso-alkanes and naphthenes ranges between 40 and 70% as determined by the EWF Standard Test Method for Analysis of Hydrocarbon Wax by Gas Chromatography. The quantitative dominance of isoalkanes (and naphthenes) determines their microcrystalline structure.
  • the solidification range is between 50 and 100 ° C according to DIN ISO 2207.
  • the needle penetration has values between 2 x 10 -1 and 160 x 10 -1 mm according to DIN 51579.
  • the solidification point and the needle penetration are used to distinguish between the microcrystalline paraffins between plastic and hard microcrystalline paraffins.
  • Soft plastic microcrystalline paraffins (so-called petrolatum) are fast with pronounced adhesiveness and have solidification points of 65 to 70 ° C and penetration values of 45 to 160 x 10 -1 mm.
  • the oil contents are between 1 and 15%.
  • Plastic microcrystalline paraffins are readily malleable and kneadable and have solidification points between 65 and 80 ° C and penetration values of 10 to 30 x 10 -1 mm.
  • the oil contents can be up to 5%.
  • the hard microcrystalline paraffins are tough and weakly adhesive with solidification points of 80 to 95 ° C and penetration values 2 to 15 x 10 -1 mm.
  • the oil contents amount to a maximum of 2% (see Ullmann's Encyclopedia of Industrial Chemistry, VCH Verlagsgesellschaft 1996 ).
  • Microcrystalline paraffins have a high molecular weight and thus high boiling points. They are so far from the residues of vacuum distillation of petroleum, especially in the production of lube oil (residue waxes), as well as from the precipitation of petroleum in its promotion, its transport and its storage won, in technologically very complex and costly process with several Stages, for example deasphalting, solvent extraction, dewaxing, de-oiling and refining.
  • the de-oiled microcrystalline paraffins contain sulfur, nitrogen and oxygen compounds as impurities. They are therefore not completely odorless and have a dark yellow to dark brown color. The refining required therefore takes place depending on the later use by bleaching (technical applications) or by hydrorefining (applications in the food and pharmaceutical industries).
  • Microcrystalline paraffins are mainly used as a mixture component in paraffin or wax mixtures.
  • the use is usually in areas up to 5%.
  • the hardness and melting point of these mixtures should be increased and flexibility and oil-binding improved.
  • Typical applications include, for example, the manufacture of waxes for impregnation, coating and laminating for the packaging and textile industries, heat seal and hot melt adhesives, and pharmaceutical and cosmetic products, including chewing gum.
  • they are used in potting and cable compounds as well as plastics in general but also in the candle, rubber and tire industries as well as in care, anti-slip and corrosion protection agents.
  • zeolites Omega zeolite, ZSN-5, X zeolite, Y zeolite and other zeolites.
  • the catalyst is based on a catalyzing metal component on a porous, heat-resistant metal oxide support (see page 2, paragraph 1), in particular 0.1 to 5 wt .-% of platinum on alumina or zeolites, such as Offretit, zeolite X, Zeolite Y, ZSM -5, ZSM-2, etc. (see page 3, center).
  • the feed to be isomerized may be any wax or waxy material, especially a Fischer-Tropsch wax (see page 5, center).
  • the hydrogen is fed to the reactor at a rate of 1,000 to 10,000 SCF / bbl and the wax at 0.1 to 10 LHSV (see page 6, center).
  • the isomerization product is liquid (see page 7, line 7). It can be fractionated by distillation or by treatment with solvents, eg with an MEK / toluene mixture (see page 7, last paragraph).
  • the entire liquid product from the isomerization unit is more advantageously treated in a second stage under mild conditions using the Group VIII noble metal isomerization catalyst and a refractory metal oxide to reduce PNA and other impurities in the isomerate and thus an improved oil To provide daylight resistance (see page 8, paragraph 2).
  • mild conditions are meant: A temperature in the range of about 170 ° to 270 ° C, a pressure of about 300 to 1500 psi, a hydrogen gas rate of about 500 to 1000 SCF / bbl and a flow rate of about 0.25 to 10 vol./vol./hr.
  • the catalyst has a decisive influence on the transformation.
  • it is based on platinum and a ⁇ -zeolite having a pore diameter of about 0.7 nm, the desired conversion to a middle distillate product is not observed, especially as the temperature decreases to 293.9 ° C. (see Example 3).
  • a process for hydroisomerization of FT paraffin is known using a zeolite based catalyst.
  • the US-A-4419220 describes the conversion of paraffin fractions in a liquid starting product by hydroisomerization and optionally cracking to liquid fractions.
  • the catalyst used is based on a B-zeolite and a metal of group VIII A.
  • Die EP 435619 A1 describes the conversion of FT paraffin to a low melting point lubricant by hydroisomerization. It is a titanium-based catalyst with a metal of VIII. Subgroup used as hydrogenation.
  • the invention has the object to provide a novel method for producing a microcrystalline paraffin.
  • microcrystalline paraffin is prepared by catalytic hydroisomerization at temperatures of 200 ° C. -300 ° C. from paraffins (FT paraffins) obtained by Fischer-Tropsch synthesis with a C chain length distribution in the range from C 20 to C 105 becomes.
  • the FT paraffins are paraffins prepared by the Fischer-Tropsch process in a known way from synthesis gas (CO and H2) in the presence of a catalyst at elevated temperature. They represent the highest-boiling fraction of the hydrocarbon mixture. The result is essentially long-chain, less branched alkanes, which are free of naphthenes and aromatics and of oxygen and sulfur compounds.
  • Such FT paraffins with a high proportion of n-paraffins and a C chain length in the range of C 20 to C 105 are converted by the method described here to high-melting, microcrystalline paraffins with a high proportion of iso-paraffins.
  • the loading of the reactor with the FT paraffin is in the range of 0.1 to 2.0, especially 0.2 to 0.8 v / v. h (volume of FT paraffin per volume of the reactor within one hour).
  • the yield of hydroisomerates is between 90 and 96% by mass, based on the particular FT paraffin used.
  • the catalytic hydroisomerization of the FT paraffins is carried out continuously in a flow-through reactor with a fixed catalyst, in particular in the form of extrudates, spheres or tablets, the reactor being oriented vertically, as desired, both top to bottom and from bottom to top can be flowed through.
  • the process may also be discontinuous in e.g. a stirred autoclave be carried out in a batch process, wherein the catalyst is contained in a permeable network or finely divided is used as granules or powder in FT paraffin.
  • the process parameters of the continuous as well as the discontinuous process are the same.
  • the degree of crystallinity is determined by an X-ray diffraction analysis. It denotes the crystalline content in the product obtained in relation to the amorphous share. The amorphous portions lead to a different diffraction of the X-rays than the crystalline portions.
  • the needle penetration at 25 ° C in the products of the invention is in the range of 20 to 160, measured according to DIN 51579. The products obtained are solid at 20 ° C, in the sense that they do not run.
  • the crystalline fraction is reduced in particular as follows: While the starting material, a crystalline content in a range of 60 to 75% occurs, is observed in the hydroisomerizate such from 30 to 45%. Especially in the range of 35 to 40 (36,37,38,39)%.
  • the crystalline fractions and the amorphous fractions are indicated by the aforementioned X-ray diffraction analysis in each case in MA.%.
  • microcrystalline paraffins produced according to the invention from FT paraffins have physical and material properties which are similar or comparable to those of petroleum-based microcrystalline paraffins (microwaxes).
  • the microcrystalline hydroisomerate prepared according to the invention and the corresponding deoiled microcrystalline hydroisomerizate, such as a microwax can be used (see introduction).
  • the resulting hydroisomerizate can also be oxidized.
  • oxidized products which differed by melting range and degree of oxidation and are used mainly as corrosion inhibitors and as a cavity and underbody protection for motor vehicles. They are also used in emulsions as care and release agents and as an additive for printing and carbon paper colorants.
  • the acid and ester groups which are statistically distributed over hydrocarbon chains, can be reacted with inorganic or organic bases to form water-dispersible formulations (emulsifying waxes) and lead to products with very good metal adhesion.
  • sunscreen waxes for the tire industry electrical insulation materials scaffolding and model waxes for the investment casting industry and wax formulation for the explosives, ammunition andkulturstatztechnik.
  • such products are suitable as release agents in the pressing of wood, chipboard and fibreboard in the manufacture of ceramic parts and because of their retention capacity for the preparation of solvent-based care products, grinding and polishing pastes and matting agents for paints.
  • these products can be used for the formulation of adhesive waxes, cheese waxes, cosmetic preparations, chewing gum bases, cast and cable compounds, sprayable pesticides, vaselines, artificial chimney logs, lubricants and hot melt adhesives.
  • An examination for food authenticity is made, for example, according to FDA, ⁇ 175. 250.
  • the hydroisomerizate is white, odorless and slightly sticky and thus differs significantly from the brittle-hard feedstock.
  • the isoalkane content is increased by about 6-fold, which is due to the increased penetration value, the decreased crystalline proportion and the reduced enthalpy of fusion is occupied.
  • the synthetic microcrystalline paraffin thus prepared is classified according to its characteristics between a plastic and a hard micron oil based on petroleum With the hydroisomerisate thus a paraffin was obtained with pronounced microcrystalline structure whose C-chain length distribution based on the carbon atoms with 23 to 91 in about that of the starting material with 27 to 95, but just shifted towards smaller chain lengths, corresponds. The chain length was determined by gas chromatography.
  • An FT paraffin having a solidification point at 70 ° C was catalytically isomerized with hydrogen at a pressure of 5 MPa (50 bar), a temperature of 250 ° C and a v / vh ratio of 0.3.
  • the structural change that occurred was confirmed by the key figures in the table.
  • the hydroisomerizate is white and odorless as well as pasty and slightly sticky.
  • the isoalkane content is increased by about 5-fold.
  • the high degree of isomerization finds expression in the significantly increased penetration value, the reduced crystalline content and the reduced enthalpy of fusion.
  • the resulting microcrystalline paraffin has a similar but slightly smaller C chain length than the FT paraffin, as evidenced by the carbon atoms: 23 to 42 in the hydroisomerate and 25 to 48 in the FT paraffin.
  • the resulting synthetic microcrystalline paraffin is comparable to a petroleum based soft plastic microcrystalline paraffin according to its characteristics.
  • Examples 1 and 2 show that the FT-paraffins, which consist predominantly of n-alkanes and have a finely crystalline structure and a brittle-hard consistency, in the non-flowing, pasty or solid paraffins that have lower melting temperatures than the feeds.
  • These paraffins are characterized by a high content of branched alkanes and consequently have a microcrystalline structure with a significantly reduced degree of crystallization and a plastic to slightly sticky consistency.
  • the branched alkanes are predominantly methylalkanes, with the methyl groups preferably occurring in the 2, 3, 4 or 5 position. To a lesser extent methyl branched alkanes were formed several times.
  • a catalyst (cylindrical extrudate, diameter 1.5 mm, length about 5 mm) was used without comminution.
  • Into the reactor tube (total volume 172 ml, inner diameter 22 mm) 92 ml of catalyst were fed undiluted.
  • the catalyst zone was also overcoated with the earth material.
  • a thermocouple was positioned in the reactor so that the temperature was measured at a depth of 2 cm and 17 cm of catalyst bed.
  • the catalysts were dried and activated (by high temperature, water is expelled and platinum is reduced).
  • the paraffin feed used was an FT paraffin C80 (solidification point 81 ° C., mass ratio n- / iso-paraffins: 93.9 / 6.1).
  • the oil content of the starting product was 0.5%.
  • the catalyst was a platinum catalyst on ⁇ -zeolite.
  • ⁇ -zeolites is referred to the reference " Atlas of Zeolites Structure Type", Elsevier Fourth Revised Edition, 1996 , pointed out.
  • Gas chromatograms obtained for this example are attached as an annex.
  • the fully synthetic microcrystalline paraffins produced by the hydroisomerization according to the invention contain no strongly branched isoalkanes, no cyclic hydrocarbons (naphthenes) and in particular no aromatics and sulfur compounds. They therefore meet the highest purity requirements for microcrystalline paraffins, making them ideally suited for use in the cosmetics and pharmaceutical industries as well as for packaging and preservation in the food industry.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Fats And Perfumes (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Cosmetics (AREA)
EP02732741.0A 2001-05-30 2002-05-31 Verfahren zur herstellung eines mikrokristallinen paraffins Expired - Lifetime EP1390329B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10126516A DE10126516A1 (de) 2001-05-30 2001-05-30 Verfahren zur Herstellung von mikrokristallinen Paraffinen
DE10126516 2001-05-30
PCT/EP2002/005970 WO2002096842A2 (de) 2001-05-30 2002-05-31 Mikrokristallines paraffin

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Publication Number Publication Date
EP1390329A2 EP1390329A2 (de) 2004-02-25
EP1390329B1 true EP1390329B1 (de) 2013-04-10

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Country Status (11)

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US (1) US7875166B2 (ru)
EP (1) EP1390329B1 (ru)
JP (1) JP2004529192A (ru)
CN (2) CN1668722B (ru)
AU (1) AU2002304654A1 (ru)
DE (1) DE10126516A1 (ru)
ES (1) ES2408810T3 (ru)
PL (1) PL203361B1 (ru)
RU (1) RU2276184C2 (ru)
WO (1) WO2002096842A2 (ru)
ZA (1) ZA200300781B (ru)

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US9206043B2 (en) 2009-02-20 2015-12-08 Marine Power Products Incorporated Method of and device for optimizing a hydrogen generating system
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PL400139A1 (pl) 2012-07-25 2014-02-03 Terra Trade Spólka Z Ograniczona Odpowiedzialnoscia Sposób otrzymywania wosków parafinowych oraz zastosowanie wosków parafinowych
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Publication number Publication date
CN101892080A (zh) 2010-11-24
CN101892080B (zh) 2012-12-19
AU2002304654A1 (en) 2002-12-09
RU2003137572A (ru) 2005-05-27
CN1668722A (zh) 2005-09-14
ZA200300781B (en) 2004-02-10
WO2002096842A2 (de) 2002-12-05
JP2004529192A (ja) 2004-09-24
ES2408810T3 (es) 2013-06-21
PL203361B1 (pl) 2009-09-30
WO2002096842A3 (de) 2003-11-13
CN1668722B (zh) 2010-05-26
EP1390329A2 (de) 2004-02-25
PL368411A1 (en) 2005-03-21
US20040192979A1 (en) 2004-09-30
RU2276184C2 (ru) 2006-05-10
DE10126516A1 (de) 2002-12-05
US7875166B2 (en) 2011-01-25

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