EP1881969A1 - Procede de stockage et de transport de carbonate de vinylene - Google Patents

Procede de stockage et de transport de carbonate de vinylene

Info

Publication number
EP1881969A1
EP1881969A1 EP06724704A EP06724704A EP1881969A1 EP 1881969 A1 EP1881969 A1 EP 1881969A1 EP 06724704 A EP06724704 A EP 06724704A EP 06724704 A EP06724704 A EP 06724704A EP 1881969 A1 EP1881969 A1 EP 1881969A1
Authority
EP
European Patent Office
Prior art keywords
vinylene carbonate
ppm
distillation
content
crystallization
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.)
Withdrawn
Application number
EP06724704A
Other languages
German (de)
English (en)
Inventor
Reinhard Langer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Saltigo GmbH
Original Assignee
Saltigo GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Saltigo GmbH filed Critical Saltigo GmbH
Publication of EP1881969A1 publication Critical patent/EP1881969A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/40—Vinylene carbonate; Substituted vinylene carbonates

Definitions

  • the present invention relates to a process for the storage and transport of vinylene carbonate (VC).
  • VC vinylene carbonate
  • Vinylene carbonate is an important intermediate for the manufacture of chemicals, pharmaceutical products, pesticides and, in particular, for polymers, paints and battery electrolytes.
  • Vinylene carbonate is prepared by known methods by splitting off hydrogen chloride from chloroethylene glycol carbonate by means of tertiary amines, in particular triethylamine.
  • Chloroethylene glycol carbonate is obtained by radical chlorination of ethylene glycol carbonate using chlorine or sulfuryl chloride.
  • Ethylene glycol carbonate was riert photochlo- means of ultraviolet light at 60-70 0 C in substance and the resulting CGC purified by vacuum distillation.
  • VC received Newman and Addor by elimination of medium triethylamine in boiling ether, the mixture being heated overnight.
  • the isolation was carried out by filtering off the triethylammonium chloride and subsequent distillation, which yielded a crude VC with 59% yield, which had to be purified by further distillation.
  • JP 2000/026449 describes the elimination in high-boiling solvents (bp. 170-300 0 C). Explicitly reacted with triethylamine in dibutyl carbonate for 20 hours at 50 0 C. After filtering off the ammonium chloride and distilling off excess triethylamine, crude VC is isolated by simple distillation. To remove traces of the amine, the VC is passed over a silica gel column. Finally, a fine distillation is carried out. The chlorine content of the VC thus obtained is given as 29 ppm, while comparative samples contain> 3000 ppm. The yield is 56%.
  • DE-A 1135452 describes the elimination of HCl from CGC at 300-400 0 C.
  • the CGC is passed in gaseous form over an inert support material which with elements of L, JJ. or VIYY. Subgroup of the periodic table or their salts or oxides is occupied.
  • the chlorides of iron, cobalt, copper, particularly preferably cadmium chloride are used.
  • Suitable support materials are pebbles and silicates with grain sizes of 4 to 8 mm.
  • the catalysts are operated as a stationary bed at atmospheric pressure or reduced pressure and a temperature of 270 to 450, preferably from 300400 0 C.
  • GB-A 899 205 describes the purification of VC produced by Newman and Addor by repeated melt crystallization. In order to obtain high molecular weight polymers one must use VC with a melting point greater than 21 ° C obtained by quadruple crystallization. Again, not directly on the purity of the VC is received, as well as the whereabouts of the mother liquors. Since the VC was prepared as described in JACS 75, 1263 (1953), distilled VC was used in the crystallization.
  • JP 2002-322171 describes the combination of distillation and crystallization for the purification of VC.
  • solvent mixtures of an aromatic component and an aliphatic hydrocarbon are claimed.
  • the yield via distillation and crystallization in the examples is 60 and 83%.
  • the purity is above 99.95%. Impurities of ethylene glycol carbonate of 400 and 25 ppm and chloride contents of 15 ppm remained in the VC.
  • a stabilizer must always be added to prevent the decomposition of VC.
  • the object of the invention is to provide a method for storage and transport of vinylene carbonate. It has surprisingly been found that VC can advantageously be stored and transported without decomposition if it is present in solid form in a high degree of purity.
  • the invention relates to a process for the storage and transport of vinylene carbonate, in which the VC has a stabilizer content of less than 100 ppm, preferably less than 10 ppm, and a purity of 99.9 to 99.99999%, preferably 99.99 to 99.9999% and is in the solid state.
  • this high-purity VC is obtained by using the VC
  • Organic compounds containing amidic nitrogen hydrogen bonds in the context of the invention are all aliphatic and aromatic carboxylic acid amides containing one or more of the following functional groups of the following formula (I)
  • R H, C 1 -C 10 -alkyl or cycloalkyl, C 6 -C 10 -aryl,
  • R, R "and R” the same or different H, Q-Cio-alkyl or cycloalkyl, C 6 -C 0 -aryl, ureas are preferably used.
  • organic compounds having amidic nitrogen hydrogen bonds from the group formamide, methylformamide, acetamide, methylacetamide, ethylacetamide, phenyl acetamide, adipamide, benzoic acid amide, phthalic acid diamide, propionamide, dimethylurea, diethylurea, diphenylurea, urea.
  • Dimethylurea, diethylurea, diphenylurea are particularly preferably used. Very particular preference is urea.
  • the thermal treatment in step a) is carried out with stirring at temperatures between 25 and 180 ° C., preferably between 60 and 160 ° C., more preferably between 90 and 140 ° C.
  • Relative to the vinylene carbonate 0.1-30% by weight, preferably 1-10% by weight, more preferably 2-6% by weight, of cleaning substance is added.
  • the addition of the organic compound with at least one amide nitrogen compound can be carried out in the presence or without the addition of solvents.
  • suitable solvents are dimethylacetamide, N-methylpyrrolidone (NMP), dimethylformamide and DMSO.
  • the vinylene carbonate is distilled off from the residue in step c). This can be done as a batch distillation from a container via a column having at least 10, preferably at least 20, more preferably at least 30 trays.
  • the low-boiling precursors of the fine distillation obtained by the process according to the invention are advantageously collected and distilled separately for the low-loss removal of those low boilers, the VC thus recovered being recycled for the thermal treatment in step a) and / or fine distillation in step b) ,
  • the VC thus obtained is subjected to melt crystallization in the process according to the invention in step a) with a content of between 99.0 and 99.99, preferably between 99.5 and 99.9%.
  • the melt crystallization can be carried out in industrial plants, as are known in the art; to name in particular tube bundle crystallizer.
  • the mother liquor obtained in the crystallization can be recycled directly into the distillation in step c) and / or thermal treatment in step a).
  • Unstabilized pure VC tends to polymerize, therefore it is marketed with stabilizers such as BHT.
  • the storage and transport of high purity, stabilizer-free VC therefore takes place at a temperature between -200 0 C and +20 0 C, preferably between 0 and 15 0 C instead.
  • the distillation apparatus consisted of an oil-heated 15L flat bottomed pot with anchor stirrer, column, reflux divider, condenser, and a constant vacuum device.
  • In front of the vacuum pump was a cooled to -78 ° C cold trap.
  • Flush pot, column, reflux condenser and condenser were made of glass, the anchor stirrer made of Teflon.
  • the column had a 1500 mm long Sulzer DX package of Hastelloy C with a diameter of 50 mm. Packages of this type have separations between 15 and 30 trays per meter.
  • the apparatus was always inertized with nitrogen before and after charging and before operation.
  • This crude VC was about 97% and had an organic and inorganic chlorine content of about 0.5% to 1%.
  • the gas chromatographic analysis was carried out by means of an HP 6890. A 50-meter-long CP-SiI 8 CB with an ID of 0.53 mm and a FD of 1.0 ⁇ m was separated.
  • Carrier gas was nitrogen at a pre-pressure of 5 psi.
  • the injector was operated with a flow of 138 ml / min and a split of 30/1. Injected was 1 ⁇ L of VC pure.
  • the injector temperature was 220 0 C, the detector temperature 320 0 C.
  • the temperature program started at 50 0 C, heated at 5 ° C / min to 25O 0 C.
  • the mixture was heated at about 35 mbar pressure to reflux and then distilled off at a reflux ratio of 30/1 forerun. Within 2.5 hours, about 160 g of distillate were obtained, so that, according to GC analysis, 96% consisted of VC. In the following 3.5 hours, about 400 g of a distillate that consisted of 97.5% of VC, followed by about 470 g of distillate with 99.4% VC content, which distilled over in 2.5 hours.
  • the cold trap had remained practically empty.
  • the crystallizer consisted of a 400 mm long thermostated glass tube with an inner diameter of 30 mm. At the lower end, a perforated disc for fixing the crystals and a drain cock for the mother liquor was attached. Under the stopcock there was a argong flushed bill of exchange. At the upper end of the gas phase could be replaced by purging with argon, also passed a coolable plastic fingers into the interior, by means of which the crystallization could be initiated targeted.
  • the educt was about 99.9% pure, had a chlorine content ⁇ 50 ppm and a water content of about 100 ppm. 24 g of feed were collected, with a content of VC of 99.87%, a chlorine content of about 110 ppm and a water content of about 230 ppm.
  • Mother liquor, flow and sweat can be recycled directly into the urea treatment or the distillation and are thus no loss.
  • Samples of vinylene carbonate purified according to Example 2 was unstabilized with exclusion of light as a liquid at 20 0 C and stored in crystalline form at 5 ° C.
  • Unstabilized vinylene carbonate samples show weak to strong yellowing and faint turbidity after 70 days.
  • Unstabilized, high-purity vinylene carbonate in the liquid state is not storage-stable.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de stockage et de transport de carbonate de vinylène. L'invention est caractérisée en ce que le carbonate de vinylène a une teneur en stabilisant inférieure à 100 ppm, et un degré de pureté de 99,9 à 99,99999 %, et se présente à l'état d'agrégat solide.
EP06724704A 2005-05-12 2006-05-04 Procede de stockage et de transport de carbonate de vinylene Withdrawn EP1881969A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005021965A DE102005021965A1 (de) 2005-05-12 2005-05-12 Verfahren zur Lagerung und zum Transport von Vinylencarbonat
PCT/EP2006/004154 WO2006119908A1 (fr) 2005-05-12 2006-05-04 Procede de stockage et de transport de carbonate de vinylene

Publications (1)

Publication Number Publication Date
EP1881969A1 true EP1881969A1 (fr) 2008-01-30

Family

ID=36603711

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06724704A Withdrawn EP1881969A1 (fr) 2005-05-12 2006-05-04 Procede de stockage et de transport de carbonate de vinylene

Country Status (7)

Country Link
US (1) US20090131687A1 (fr)
EP (1) EP1881969A1 (fr)
JP (1) JP2008540468A (fr)
KR (1) KR20080008420A (fr)
CN (1) CN101175744A (fr)
DE (1) DE102005021965A1 (fr)
WO (1) WO2006119908A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101717388B (zh) * 2009-10-29 2012-06-27 张家港市华盛化学有限公司 抑制碳酸亚乙烯酯变色的方法
CN102002032B (zh) * 2010-10-30 2013-04-17 江苏华盛精化工股份有限公司 抑制碳酸亚乙烯酯变质的方法
WO2016009793A1 (fr) * 2014-07-14 2016-01-21 宇部興産株式会社 Carbonate de vinylène de haute pureté, solution électrolytique non aqueuse et dispositif d'accumulation d'énergie électrique la comprenant
CN106632224B (zh) * 2016-11-07 2019-04-26 惠州市宙邦化工有限公司 一种亚甲基碳酸乙烯酯的制备方法
CN112480060B (zh) * 2020-11-30 2022-04-01 苏州华一新能源科技股份有限公司 一种乙烯基碳酸乙烯酯的储存方法

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Publication number Priority date Publication date Assignee Title
JP4255228B2 (ja) * 2000-11-29 2009-04-15 三菱化学株式会社 高純度ビニレンカーボネートの製造方法
JP5150989B2 (ja) * 2001-04-25 2013-02-27 三菱化学株式会社 高純度ビニレンカーボネートの製造方法
JP2002346303A (ja) * 2001-05-28 2002-12-03 Mitsubishi Chemicals Corp 晶析方法

Non-Patent Citations (1)

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Title
See references of WO2006119908A1 *

Also Published As

Publication number Publication date
WO2006119908A1 (fr) 2006-11-16
US20090131687A1 (en) 2009-05-21
DE102005021965A1 (de) 2006-11-16
CN101175744A (zh) 2008-05-07
KR20080008420A (ko) 2008-01-23
JP2008540468A (ja) 2008-11-20

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