WO1998056758A1 - Procede pour la production d'isocyanates organiques - Google Patents

Procede pour la production d'isocyanates organiques Download PDF

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Publication number
WO1998056758A1
WO1998056758A1 PCT/EP1998/003224 EP9803224W WO9856758A1 WO 1998056758 A1 WO1998056758 A1 WO 1998056758A1 EP 9803224 W EP9803224 W EP 9803224W WO 9856758 A1 WO9856758 A1 WO 9856758A1
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WIPO (PCT)
Prior art keywords
organic
catalyst
organic solvent
process according
reaction
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PCT/EP1998/003224
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English (en)
Inventor
Richard Colin Smith
Jeremy Charles Bausor Hunns
Original Assignee
Huntsman Ici Chemicals Llc
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 Huntsman Ici Chemicals Llc filed Critical Huntsman Ici Chemicals Llc
Priority to AU82117/98A priority Critical patent/AU8211798A/en
Publication of WO1998056758A1 publication Critical patent/WO1998056758A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C263/00—Preparation of derivatives of isocyanic acid
    • C07C263/04—Preparation of derivatives of isocyanic acid from or via carbamates or carbamoyl halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to a multi-step process for the production of organic isocyanates from amines and organic carbonates using a common solvent.
  • US-A 5.315.034 discloses a muitistep process for the preparation of alkyl mono- and diisocyanates by reacting the corresponding aliphatic amine or diamine with dimethylcarbonate in the presence of a basic catalyst, neutralising the catalyst, removing the alcohol and any excess of dimethylcarbonate, partially vaporizing and converting the urethane groups thus formed into isocyanate groups by cracking, subjecting the cracking products to fractional distillation at reduced pressure and optionally recycling the unconverted part to the partial vaporization step.
  • the described method involves vaporization of the urethanes and fractional distillation at reduced pressure and hence does not allow for the preparation of involatile isocyanates.
  • EP-A 323.514 describes a two-step reaction for the preparation of diisocyanates consisting of first reacting a diamine and dimethylcarbonate in the presence of an alkali catalyst and then thermally decomposing the thus formed urethane compound in a high boiling solvent under reduced pressure in the presence of a specific metal catalyst to obtain a diisocyanate compound.
  • the second step of this reaction requires the presence of a specific catalyst and a high boiling solvent and is carried out under reduced pressure.
  • the process can only be used for the production of difunctional isocyanates.
  • DE-A 4.413.580 a method for preparing 1 ,4-diisocyanatobutane is described by converting 1,4-butanediamine into the corresponding dialkyl- or diarylurethanes which are subsequently thermally cracked at a temperature of between 100 and 600 °C into 1 ,4-diisocyanatobutane and an alcohol, with fractional condensation of the cracking products.
  • the invention thus concerns a process for the production of organic isocyanates comprising the following steps : (1) reacting an amine compound with an organic carbonate in the presence of a catalyst and an organic solvent;
  • the invention thus provides an efficient process for making any organic isocyanate, including higher boiling isocyanates.
  • Amine compounds which can be used in step (1) of the present process include aliphatic, cycloaliphatic or aromatic mono-, di- or polyamines.
  • Suitable amines include, for example, methylamine, ethylamine, n-propyl amine, isopropylamine, n-butylamine, isobutyiamine, hexylamine, cyclopropyl amine, cyclobutylamine, cyclohexylamine, laurylamine, stearylamine, phenyl amine, 4-chlorophenyiamine, 2-fluorophenyl amine, 3,4-dichlorophenylamine, aniline, benzylamine, tolylamine, diisopropyl phenylamine, 2,4'-diamino diphenylmethane, 4,4'-diaminodiphenylmethane, 2,2'-diaminodiphenylmethane and higher homologs (polyaminopolyphenylmethanes), 2,4-toluenediamine, 2,6-toluenediamine, m-
  • aromatic di- or polyamines like toluenediamines, diaminodiphenylmethanes or polyaminopolyphenylmethanes or any mixtures thereof.
  • Suitable organic carbonates include cyclic or alicyclic carbonates such as, for example, ethylene carbonate, propylene carbonate, styrene carbonate, diphenyl carbonate, methyl phenyl carbonate.dimethyl carbonate, diethyl carbonate, dipropyl carbonate, dibutyl carbonate, dihexyl carbonate, methyl ethyl carbonate, methyl butyl carbonate and the like.
  • the polyamines and the organic carbonates may be reacted in stoichiometric quantities.
  • the type of catalyst used in step (1) is not critical. Suitable catalysts include heterogeneous base catalysts.
  • a preferred class of catalysts however are metal based catalysts.
  • Organic or inorganic salts including, for example, acetates, chlorides, nitrates, propionates, isopropanoates, butanoates, 2-ethylhexanoates, n-octoates, isononanoates, benzoates, chlorobenzoates, naphthenates, stearates, itaconates, pivalates, phenolates, acetylacetonates, alkoxides, C 16 /C 18 -alkenylsuccinoates (ASA), C 12 -alkenylsuccinoates (DSA), and the like, of metals may be used.
  • ASA alkenylsuccinoates
  • DSA C 12 -alkenylsuccinoates
  • alkanoates having from 1 to 15 carbon atoms.
  • Suitable catalysts include, for example, zinc catalysts such as zinc chloride, zinc acetate, zinc nitrate, zinc propionate, zinc octoate, zinc benzoate, zinc p-chiorobenzoate, zinc naphthenate, zinc stearate, zinc itaconate, zinc pivalate, zinc phenolate, zinc acetylacetonate, zinc methoxide, lead catalysts like lead acetate, lead nitrate and lead octoate, and tin catalysts like stannous chloride, stannous octoate, and mixtures thereof.
  • zinc catalysts such as zinc chloride, zinc acetate, zinc nitrate, zinc propionate, zinc octoate, zinc benzoate, zinc p-chiorobenzoate, zinc naphthenate, zinc stearate, zinc itaconate, zinc pivalate, zinc phenolate, zinc acetylacetonate, zinc methoxide, lead catalysts like lead acetate, lead
  • the metal in the catalyst is selected from the group consisting of Ti, Zr, Mn, Fe, Co, Ni, Cu, Zn, Sn, Pb, Bi and Cd.
  • the catalyst in step (1 ) is generally used in amounts between 10 "3 and 20 mole% based on the amount of amines used.
  • step (1 ) The reaction conditions in step (1 ) largely depend on the type of reactants used, but are chosen so that substantially all of the amines are converted into a mixture of carbamates and alcohols.
  • Step (1 ) may be carried out at atmospheric or superatmospheric pressures.
  • reaction time for step (1 ) will normally not exceed 5 hours. Reaction times of less than 3 hours are common, and reaction times of less than 2 hours have been achieved without any problem.
  • reaction temperature in step (1 ) will be between 50 and 300°C.
  • the method of the invention is carried out at temperatures between 100 and 250°C.
  • the catalyst needs to be removed from the reaction mixture before initiating step (3). It may be removed continuously during, or after the termination of step (1 ) by any suitable method.
  • a preferred separation method for step (2) is filtration.
  • any excess reactants and/or by-products from step (1 ) may need to be removed as well before proceeding to step (3).
  • the type of organic isocyanates obtained in step (3) depends on the type of the amine compound used in step (1) and may be monomeric, di- or polymeric isocyanates.
  • monomeric isocyanates which may be formed include methyl isocyanate, ethylisocyanate, isopropylisocyanate, isobutylisocyanate, hexylisocyanate, cyclohexylisocyanate, laurylisocyanate, stearyl isocyanate, phenylisocyanate, 4-chlorophenylisocyanate, 2-fluorophenylisocyanate, 3,4-dichlorophenyl isocyanate, tolylisocyanate and diisopropyl phenylisocyanate.
  • difunctional isocyanates which can be made according to the present method include diphenylmethane diisocyanates such as 4,4'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, 2,2'-diphenyl methane diisocyanate and mixtures thereof, toluene diisocyanates such as 2,4-toluene diisocyanate, 2,6-toluene diisocyanate and mixtures thereof, m-phenylene diisocyanate, 1 ,4-butylene diisocyanate, 1 ,6-hexylene diisocyanate, 1 ,5-naphthylene diisocyanate, 1 ,4-cyclohexylene diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, 1 ,4-xylylene diisocyanate and isophorone diisocyanate.
  • Trifunctional and higher functional isocyanates which can be made include 2,4,6-toluene triisocyanate and polymethylene polyphenylene polyisocyanates.
  • any mixtures of mono-, di- and polyfunctional isocyanates may be obtained depending on the composition of the starting amine compound.
  • step (3) a solution of the carbamate formed in step (1 ) in the organic solvent is subjected to thermal decomposition.
  • the solvent is the organic carbonate used in the reaction of step (1).
  • any solvent or mixture of solvents which is inert to the reactants under the reaction conditions may be employed.
  • Suitable solvents which may be employed include, for example, aromatic hydrocarbons such as benzene, halogenated aromatic hydrocarbons such as monochlorobenzene, ortho-dichlorobenzene or 1-chloronaphthalene, alkylated aromatic hydrocarbons like toluene, xylene, ethylbenzene, cumene or tetrahydronaphthalene, other functionalised aromatic hydrocarbons such as anisol, diphenylether, ethoxybenzene, benzonitrile, 2-fluoroanisole, 2,3-dimethylanisole or trifluorotoluene, alkanes such as n-pentane, n-hexane, n-heptane or higher or branched alkanes, cyclic alkanes like cyclopentane, cyclohexane or derivatives thereof, halogenated alkanes like chloroform, dichloromethane, carbontetrach
  • step (3) The use of low boiling solvents in step (3) is advantageous as it facilitates the removal by distillation afterwards.
  • Preferred solvents other than the organic carbonate used in step (1 ) comprise monochlorobenzene or ortho-dichlorobenzene.
  • the excess organic carbonate remaining after step (1 ) may be removed before initiating step (3).
  • reaction conditions in step (3) depend on the type of reactants used and the type of solvent.
  • the process may be carried out at atmospheric or superatmospheric pressures.
  • reaction time for step (3) is dependent on the temperature and on the type and quantity of the carbamate compound, but will normally not exceed 5 hours. Reaction times of less than 3 hours are common, and reaction times of less than 2 hours have been achieved without any problem.
  • the reaction temperature in step (3) is generally between 100 and 400 °C, preferably between 200 and 300 oC.
  • the distillation in step (4) can be conducted in any distillation apparatus which can be equipped, if required, with heating and/or cooling means to keep the temperature within the desired range.
  • the process of the present invention may be conducted batchwise or as a semi-continuous or continuous process.
  • the isocyanates and alcohols obtained by this process are generally of high purity and no additional treatment is required to further purify said products. However, if a particularly high grade of purity is required, the reaction products formed may be subjected to known purification methods, such as filtration, extraction, recrystallisation or distillation.
  • the invention is illustrated by the following example.
  • the methyl urethane of polyphenylene polymethylene polyamine was prepared as follows:
  • polyphenylene polymethylene polyamine (4.8 g; 24.2 mmol) was weighed into a clean dry glass liner. The solid was then dissolved in o-dichlorobenzene (ODCB)(80 ml) and dimethyl carbonate added (21.6 g; 240 mmol) along with the catalyst (lead octoate as an 18 % w/w solution in mineral oil; 1.04 g equivalent to 0.9 mmol Pb). The glass liner was then placed inside a standard 300 ml stainless steel autoclave and the autoclave sealed. The reaction vessel was then purged with nitrogen and the contents heated to 180 C for 2 hours. At the end of the reaction period the contents were cooled and recovered. Four identical experiments were carried out and the crude product solutions bulked together for post reaction treatment.
  • ODCB o-dichlorobenzene
  • the solution was filtered to remove catalyst residues and the excess dimethyl carbonate and any residual methanol by-product were stripped from the crude mixture in vacuo.
  • the resulting solution was washed with aqueous HCI (1 M/l) then washed twice with water before being dried over magnesium sulphate.
  • the yield was 10 g of polymethylene polyphenylene poly(methylurethane) as a 2% w/w solution in ODCB.
  • thermolysis reactor 200 ml of the above solution was transferred to the thermolysis reactor.
  • the reactor was sealed and purged with nitrogen.
  • the polymethylene polyphenylene poly(methylurethane) was thermolysed at 250 C for 45 mins at 5 bar pressure with a nitrogen purge equivalent to 1 l/min.
  • ODCB solvent distilled from the reactor at a rate of 10 g/min and this was replaced at the same rate with fresh solvent.
  • the resulting polymethylene polyphenylene polyisocyanate was recovered by distillation of the solvent yielding a crude product with an NCO v of 9.4 % w/w.

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

Abstract

L'invention concerne un procédé de production d'isocyanates organiques. Ce procédé comprend les étapes consistant à (1) faire réagir un composé d'amine avec un carbonate organique en présence d'un catalyseur et d'un solvant organique; (2) retirer le catalyseur; (3) décomposer thermiquement la solution du carbamate formé au cours de l'étape (1) dans ledit solvent organique; et (4) séparer le solvant organique/le mélange d'alcool ainsi obtenu de l'isocyanate organique formé au cours de l'étape (3) par distillation.
PCT/EP1998/003224 1997-06-09 1998-05-29 Procede pour la production d'isocyanates organiques WO1998056758A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU82117/98A AU8211798A (en) 1997-06-09 1998-05-29 Process for the production of organic isocyanates

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP97109295 1997-06-09
EP97109295.2 1997-06-09

Publications (1)

Publication Number Publication Date
WO1998056758A1 true WO1998056758A1 (fr) 1998-12-17

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WO (1) WO1998056758A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001056977A1 (fr) * 2000-02-03 2001-08-09 Enichem S.P.A. Procede integre de preparation d'isocyanates aromatiques et procedures utilisees pour effectuer les phases intermediaires associees
WO2002024634A2 (fr) * 2000-09-19 2002-03-28 Arco Chemical Technology, L.P. Procede sans phosgene destine a produire des isocyanates organiques
CN100369671C (zh) * 2005-12-01 2008-02-20 中国科学院山西煤炭化学研究所 环己烷丁酸锌用于制备n-取代氨基甲酸酯的方法
CN100408557C (zh) * 2003-08-26 2008-08-06 河北工业大学 一种制备2，4-甲苯二氨基甲酸甲酯的方法
US7423171B2 (en) 2006-06-20 2008-09-09 Repsol Ypf, S.A. One-step catalytic process for the synthesis of isocyanates
EP2036884A1 (fr) 2007-09-14 2009-03-18 Repsol Ypf S.A. Procédé pour la fabrication d'isocyanates et carbamates de fluorés
WO2009115538A1 (fr) 2008-03-18 2009-09-24 Basf Se Procédé de fabrication d'uréthanes à partir d'amines aromatiques monofonctionnelles et difonctionnelles
WO2009115539A1 (fr) 2008-03-18 2009-09-24 Basf Se Carbamates métalliques à base de tolylène-diamines
EP2213658A1 (fr) * 2007-11-19 2010-08-04 Asahi Kasei Chemicals Corporation Procédé de fabrication d'un isocyanate et d'un composé hydroxylé aromatique
US8519174B2 (en) 2008-03-18 2013-08-27 Basf Se Metal carbamates formed from diaminophenylmethane
US8729291B2 (en) 2008-08-22 2014-05-20 Basf Se Method for producing urethanes composed of di-functional aromatic amines and dialkyl carbonates
EP2275405A4 (fr) * 2008-05-15 2015-10-28 Asahi Kasei Chemicals Corp Procédé de production d isocyanate utilisant un diaryl carbonate
CN108395384A (zh) * 2018-04-09 2018-08-14 辽宁科技学院 异氰酸酯的绿色合成方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0323514A1 (fr) * 1987-01-13 1989-07-12 Daicel Chemical Industries, Ltd. Procede de preparation de composes d'isocyanate
EP0510459A2 (fr) * 1991-04-23 1992-10-28 Bayer Ag Procédé de préparation de poly(o-alkyluréthanes) de la série des diphénylméthanes
EP0520273A2 (fr) * 1991-06-27 1992-12-30 Bayer Ag Procédé pour la préparation de bis(éthoxy carbonylamino) toluols et leur utilisation dans la préparation de diisocyanatotoluols
US5315034A (en) * 1992-05-15 1994-05-24 Enichem Synthesis S.P.A. Procedure for the preparation of alkyl isocyanates
DE4413580A1 (de) * 1994-04-19 1995-10-26 Bayer Ag Verfahren zur Herstellung von 1,4-Diisocyanatobutan (BDI)

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0323514A1 (fr) * 1987-01-13 1989-07-12 Daicel Chemical Industries, Ltd. Procede de preparation de composes d'isocyanate
EP0510459A2 (fr) * 1991-04-23 1992-10-28 Bayer Ag Procédé de préparation de poly(o-alkyluréthanes) de la série des diphénylméthanes
EP0520273A2 (fr) * 1991-06-27 1992-12-30 Bayer Ag Procédé pour la préparation de bis(éthoxy carbonylamino) toluols et leur utilisation dans la préparation de diisocyanatotoluols
US5315034A (en) * 1992-05-15 1994-05-24 Enichem Synthesis S.P.A. Procedure for the preparation of alkyl isocyanates
DE4413580A1 (de) * 1994-04-19 1995-10-26 Bayer Ag Verfahren zur Herstellung von 1,4-Diisocyanatobutan (BDI)

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001056977A1 (fr) * 2000-02-03 2001-08-09 Enichem S.P.A. Procede integre de preparation d'isocyanates aromatiques et procedures utilisees pour effectuer les phases intermediaires associees
US6992214B2 (en) * 2000-02-03 2006-01-31 Dow Global Technologies Inc. Integrated process for the preparation of aromatic isocyanates and procedures for effecting the relative intermediate phases
CN1330629C (zh) * 2000-02-03 2007-08-08 陶氏环球技术公司 制备芳烃异氰酸酯的综合方法及实施相关中间阶段的程序
WO2002024634A2 (fr) * 2000-09-19 2002-03-28 Arco Chemical Technology, L.P. Procede sans phosgene destine a produire des isocyanates organiques
WO2002024634A3 (fr) * 2000-09-19 2002-05-30 Arco Chem Tech Procede sans phosgene destine a produire des isocyanates organiques
US6781010B1 (en) 2000-09-19 2004-08-24 Lyondell Chemical Company Non-phosgene route to the manufacture of organic isocyanates
CN100408557C (zh) * 2003-08-26 2008-08-06 河北工业大学 一种制备2，4-甲苯二氨基甲酸甲酯的方法
CN100369671C (zh) * 2005-12-01 2008-02-20 中国科学院山西煤炭化学研究所 环己烷丁酸锌用于制备n-取代氨基甲酸酯的方法
US7423171B2 (en) 2006-06-20 2008-09-09 Repsol Ypf, S.A. One-step catalytic process for the synthesis of isocyanates
EP2036884A1 (fr) 2007-09-14 2009-03-18 Repsol Ypf S.A. Procédé pour la fabrication d'isocyanates et carbamates de fluorés
EP2213658A1 (fr) * 2007-11-19 2010-08-04 Asahi Kasei Chemicals Corporation Procédé de fabrication d'un isocyanate et d'un composé hydroxylé aromatique
EP2213658A4 (fr) * 2007-11-19 2013-12-04 Asahi Kasei Chemicals Corp Procédé de fabrication d'un isocyanate et d'un composé hydroxylé aromatique
EP2792673A1 (fr) * 2007-11-19 2014-10-22 Asahi Kasei Chemicals Corporation Dérivés d'esters carbamiques pour la préparation de composés isocyanates et hydroxyphényles
US8703989B2 (en) 2007-11-19 2014-04-22 Asahi Kasei Chemicals Corporation Isocyanates and aromatic hydroxy compounds
US8519174B2 (en) 2008-03-18 2013-08-27 Basf Se Metal carbamates formed from diaminophenylmethane
WO2009115539A1 (fr) 2008-03-18 2009-09-24 Basf Se Carbamates métalliques à base de tolylène-diamines
US8481777B2 (en) 2008-03-18 2013-07-09 Basf Se Metal carbamates formed from tolylenediamines
US8846970B2 (en) 2008-03-18 2014-09-30 Basf Se Metal carbamates formed from tolylenediamines
US8846971B2 (en) 2008-03-18 2014-09-30 Basf Se Metal carbamates formed from diaminophenylmethane
WO2009115538A1 (fr) 2008-03-18 2009-09-24 Basf Se Procédé de fabrication d'uréthanes à partir d'amines aromatiques monofonctionnelles et difonctionnelles
US8921598B2 (en) 2008-03-18 2014-12-30 Basf Se Method for producing urethanes composed of mono and di-functional aromatic amines
EP2275405A4 (fr) * 2008-05-15 2015-10-28 Asahi Kasei Chemicals Corp Procédé de production d isocyanate utilisant un diaryl carbonate
US8729291B2 (en) 2008-08-22 2014-05-20 Basf Se Method for producing urethanes composed of di-functional aromatic amines and dialkyl carbonates
CN108395384A (zh) * 2018-04-09 2018-08-14 辽宁科技学院 异氰酸酯的绿色合成方法

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