2-chloro-2-methylbutane

Hydrolysis

Administrative data

Endpoint:

hydrolysis

Type of information:

experimental study

Adequacy of study:

supporting study

Study period:

1934

Reliability:

4 (not assignable)

Rationale for reliability incl. deficiencies:

documentation insufficient for assessment

Data source

Reference

Reference 1

Title:

The Hydrolysis of Tertiary Aliphatic Halides

Author:

Woodburn HM, Whitmore FC

Year:

1934

Bibliographic source:

Journal of the American Chemical Society 56, 1394-1395.

Reference 2

Title:

Hydrolysis of Secondary and Tertiary Alkyl Halides

Author:

Hughes ED

Year:

1935

Bibliographic source:

Journal of the American Chemical Society 57, 708-709.

Materials and methods

Test guideline

Qualifier:

no guideline followed

Principles of method if other than guideline:

Principle of test: The hydrolysis of tertiary aliphatic halides were examined. A specific amounts of the test substance and water or the aqueous reagents were stirred. The resulting inorganic halide was measured by tritation with silver nitrate. Furthermore a mechanism for the reaction was proposed.

GLP compliance:

no

Remarks:

Test conducted before GLP.

Test material

Test material information

Constituent 1

Reference substance name:

2-chloro-2-methylbutane

EC Number:

209-836-2

EC Name:

2-chloro-2-methylbutane

Cas Number:

594-36-5

Molecular formula:

C5H11Cl

IUPAC Name:

2-chloro-2-methylbutane

Test material form:

liquid

Study design

Details on sampling:

Titration with silver nitrate and potassium thiocyanate according to Vollhard to measure the inorganic halide.

Results and discussion

Dissipation DT50 of parent compound

Dissipation DT50 of parent compound 1

pH:

4

Dissipation DT50 of parent compound 2

pH:

7

Dissipation DT50 of parent compound 3

pH:

9

Details on results:

Hughes (1935) suggested a SN1 and E1 mechanism.

Any other information on results incl. tables

50 ml Amylchloride shaken with 100 ml water in the cold: 0.3% hydrolysis  after 2 min, 
125 ml substance stirred with 125 ml water cold: 240 min: 24.2%, 540 min  54.8%.
With 100 ml water stirred cold: 180 min: 0.1%, 420 min 1.2%, 870 min 16%. 

50 ml substance with 100 ml Water, Reflux, 540 min: 48.6 % reacted; with stirring: 450 min : 81.8%  reacted

50 ml substance with 100 ml 5% Na2CO3, reflux, 540 min: 44.5 % reacted, with stirring: 480 min: 81.1  % reacted
50 ml substance with 100 ml 40% Na2CO3, reflux, 1020 min: 20% reacted.
50 ml substance with 100 ml 2% H2SO4, reflux, 540 min: 46.8 % reacted

125 ml Amylchloride with 1.4 N NaOH (125 ml) stirred cold: 240 min 23%,  540 min 60%., wiht 100 ml 1.4 N NaOH: 420 min 2.8%, 870 min 14.8%.
Reaction product was and tert-Amylalcohol. 

Hughes (1935)identified the mechanism was identified as unimolecular SN1 and E1 reaction.

The hydrolysis of the substance showed alomst similar velocity regardless of dilution in sodium carbonate, water or sulfuric acid. The velocity in alkaline solution is 3.00 average changes in titer per hour and the velocity in acid solution is 3.12 average changes in titer per hour (in relation to 0.005 N acid and alkali).

Applicant's summary and conclusion

Validity criteria fulfilled:

not applicable

Conclusions:

The examination of hydrolysis of the test substance showed that inorganic halid and alcohol or the olefin is formed in aqueous solution.