EP0085949B1 - Trichloroéthène stabilisé et additif pour stabiliser le trichloréthène - Google Patents

Trichloroéthène stabilisé et additif pour stabiliser le trichloréthène Download PDF

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Publication number
EP0085949B1
EP0085949B1 EP83101002A EP83101002A EP0085949B1 EP 0085949 B1 EP0085949 B1 EP 0085949B1 EP 83101002 A EP83101002 A EP 83101002A EP 83101002 A EP83101002 A EP 83101002A EP 0085949 B1 EP0085949 B1 EP 0085949B1
Authority
EP
European Patent Office
Prior art keywords
ppm
tert
weight
trichloroethene
hydroxyanisole
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
EP83101002A
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German (de)
English (en)
Other versions
EP0085949A2 (fr
EP0085949A3 (en
Inventor
Klaus Dr. Dipl.-Chem. Blum
Rudolf Dr. Dipl.-Chem. Strasser
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.)
Wacker Chemie AG
Original Assignee
Wacker Chemie AG
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 Wacker Chemie AG filed Critical Wacker Chemie AG
Priority to AT83101002T priority Critical patent/ATE53565T1/de
Publication of EP0085949A2 publication Critical patent/EP0085949A2/fr
Publication of EP0085949A3 publication Critical patent/EP0085949A3/de
Application granted granted Critical
Publication of EP0085949B1 publication Critical patent/EP0085949B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/261—Alcohols; Phenols
    • C11D7/262—Alcohols; Phenols fatty or with at least 8 carbon atoms in the alkyl or alkenyl chain
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5004—Organic solvents
    • C11D7/5018—Halogenated solvents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
    • D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/24—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/266—Esters or carbonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/28—Organic compounds containing halogen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3281—Heterocyclic compounds

Definitions

  • a commonly used, well stabilizing additive for trichlorethylene is butylene oxide.
  • Stabilizing mixtures containing nitriles, such as propionitrile, acrylonitrile and the like, have also proven useful for trichlorethylene, which is used as an auxiliary for paints.
  • GB-A-932,138 claims a stabilizer system for trichlorethylene which contains as components an organic amine, an epoxy compound and a quaternary ammonium salt.
  • the replacement of carcinogenic butylene oxide by non-toxic epoxides is not described, but in all examples, butylene oxide is emphasized.
  • Example 2 describes a stabilizer mixture of butylene oxide, triethylamine, cetyltrimethylammonium bromide or trimethylammonium chloride, isopropanol, N-methylpyrrole and diisobutylene.
  • a disadvantage of this stabilizer mixture is the addition of the quaternary ammonium salt described as essential, since these compounds cause severe corrosion when the stabilized trichlorethylene is applied.
  • FR-A 1 233 249 describes a stabilizer mixture of amine and a combination of two different epoxides, the one being selected from butylene oxide, propylene oxide and 2-methylbutene oxide, the other styrene oxide, a-methylstyrene oxide, a-pinene oxide, lime mono- or can be dioxide.
  • the problem of the use of toxic butylene oxide and its substitution by non-toxic epoxides is not described. Rather, Table (111) teaches substitution of butylene or propylene oxide.
  • the object of the invention was to provide means for stabilizing trichlorethylene and thus stabilized trichlorethylene which does not contain the stabilizing additives mentioned above. Furthermore, it was an object of the invention to find agents for stabilizing trichlorethylene which can make appropriately formulated trichlorethylene suitable both as an auxiliary for paints and as a degreasing agent.
  • the invention furthermore relates to stabilized trichorethylene which contains the stabilizer mixture according to the invention.
  • the amount of stabilizer is generally between 3,200 and 25,000 ppm by weight, preferably 5,000 to 10,000 ppm by weight, in each case based on the total amount of stabilized trichloroethene.
  • Amines boiling between 70 and 110 ° C at 1 bar are equivalent to diisopropylamine in the context of the invention. Examples of these are triethylamine and dimethylisobutylamine.
  • the proportion of epoxides is preferably 4,000 to 6,000 ppm by weight.
  • the BAM test was unresponsive.
  • the accelerated oxidation test according to MIL-T-81533 A gave one. Service life of 1920 hours.
  • the pH was 9.5 after 48 hours.
  • the test liquid was colorless.
  • the service life until the acidity limit of 0.02% by weight of HCl was reached was 240 hours.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Textile Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (4)

1. Produit pour stabiliser le trichloréthène, produit caractérisé par l'association des constituants suivants:
a) le N-méthyl-pyrrole et/ou le tert-butyl-2 phénol et/ou le ditert-butyl-2,4 phénol et/ou l'hydroxy-4- anisole et/ou le tert-butyl-2 hydroxy-4 anisole et/ou le tert-butyl-3 hydroxy-4-anisole et/ou le diméthyl-2,6 phénol,
b) le méthyl-2 époxy 2,3 butane et/ou le diméthl-2,3 époxy-2,3 butane et/ou le diméthyl-3,3 époxy-1,2 butane et/ou l'époxy-1,2 pentane et/ou l'oxyde de cyclopentène,
c) le di-isobutylène,
d) l'acétate d'éthyle et/ou l'acétate de propyle,
e) au moins une amine qui boute entre 70 et 110°C sous 1 bar.
2. Trichloréthène stabilisé caractérisé en ce qu'il contient un produit selon la revendication 1.
3. Trichloréthène selon la revendication 2, caractérisé en ce qu'il contient de 3.200 à 25.000 ppm en poids du produit de stabilisation.
4. Trichloréthène selon la revendication 3 qui contient:
(a1) de 0 à 500 ppm en poids de N-méthyl-pyrrole,
(a2) de 0 à 500 ppm en poids de tert-butyl-2 phénol et/ou de ditert-butyl-2,4 phénol et/ou d'hydroxy-4 anisole et/ou de tert-butyl-2 hydroxy-4 anisole et/ou de tert-butyl-2 hydroxy-4 anisole et/ou de tert-butyl-3 hydroxy-4 anisole et/ou de diméthyl-2,6 phénol,
avec la condition que les composantes a1 et a2 soient présentes en une quantité d'au moins 10 ppm en poids,
(b) de 1.000 à 8.000 ppm en poids de méthyl-2 époxy-2,3 butane et/ou de diméthyl-2,3 époxy-2,3 butane et/ou de diméthyl-3,3 époxy-1,2 butane et/ou d'époxy-1,2 pentane et/ou d'oxyde de cyclopentène,
(c) 100 à 4.000 ppm en poids de di-isobutylène,
(d) de 2.000 à 3.000 ppm en poids d'acétate d'éthyle et/ou d'acétate de propyle,
(e) de 10 à 100 ppm en poids de di-isopropylamine et/ou de triéthylamine et/ou de diméthyl- isobutylamine.
EP83101002A 1982-02-05 1983-02-03 Trichloroéthène stabilisé et additif pour stabiliser le trichloréthène Expired - Lifetime EP0085949B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT83101002T ATE53565T1 (de) 1982-02-05 1983-02-03 Stabilisiertes trichlorethen und mittel zur stabilisierung von trichlorethen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19823203907 DE3203907A1 (de) 1982-02-05 1982-02-05 Stabilisiertes trichlorethen und mittel zur stabilisierung von trichlorethen
DE3203907 1982-02-05

Publications (3)

Publication Number Publication Date
EP0085949A2 EP0085949A2 (fr) 1983-08-17
EP0085949A3 EP0085949A3 (en) 1984-07-18
EP0085949B1 true EP0085949B1 (fr) 1990-06-13

Family

ID=6154849

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83101002A Expired - Lifetime EP0085949B1 (fr) 1982-02-05 1983-02-03 Trichloroéthène stabilisé et additif pour stabiliser le trichloréthène

Country Status (5)

Country Link
EP (1) EP0085949B1 (fr)
JP (1) JPS58135827A (fr)
AT (1) ATE53565T1 (fr)
CA (1) CA1175220A (fr)
DE (2) DE3203907A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2001296504A1 (en) * 2000-11-03 2002-05-15 Dow Global Technologies Inc. Stabilizer and solvent compositions
KR100754721B1 (ko) * 2002-04-26 2007-09-03 삼성전자주식회사 직교주파수분할다중화 통신시스템에서 다중화 데이터 송수신 장치 및 방법
FR2861390B1 (fr) * 2003-10-24 2006-01-21 Arkema Stabilisation du trans-1,2-dichlorethylene

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2797250A (en) * 1954-05-13 1957-06-25 Du Pont Stabilization of chlorinated hydrocarbons
BE563604A (fr) * 1957-11-09
DE1136695B (de) * 1957-11-15 1962-09-20 Sicedison Spa Stabilisieren von Trichloraethylen gegen Zersetzung
FR1233249A (fr) * 1958-08-15 1960-10-12 Canadian Ind Stabilisation des halohydrocarbures, en particulier pour empêcher la décomposition du trichloroéthylène
GB932138A (en) * 1960-10-27 1963-07-24 Canadian Ind Stabilization of halogenated hydrocarbons used as metal degreasing solvents
JPS494448B1 (fr) * 1970-12-23 1974-02-01

Also Published As

Publication number Publication date
DE3381638D1 (de) 1990-07-19
DE3203907A1 (de) 1983-08-11
CA1175220A (fr) 1984-10-02
EP0085949A2 (fr) 1983-08-17
JPS58135827A (ja) 1983-08-12
EP0085949A3 (en) 1984-07-18
ATE53565T1 (de) 1990-06-15
JPS6121604B2 (fr) 1986-05-28

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