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Dimethyl Trisulfide Synthesis Essay

17.1.2017   

EN

Official Journal of the European Union

L 13/186


COMMISSION IMPLEMENTING REGULATION (EU) 2017/62

of 14 December 2016

concerning the authorisation of 3-(methylthio) propionaldehyde, methyl 3-(methylthio) propionate, allylthiol, dimethyl sulfide, dibutyl sulfide, diallyl disulfide, diallyl trisulfide, dimethyl trisulfide, dipropyl disulfide, allyl isothiocyanate, dimethyl disulfide, 2-methylbenzene-1-thiol, S-methyl butanethioate, allyl methyl disulfide, 3-(methylthio) propan-1-ol, 3-(methylthio) hexan-1-ol, 1-propane-1-thiol, diallyl sulfide, 2,4-dithiapentane, 2-methyl-2-(methyldithio) propanal, 2-methylpropane-1-thiol, methylsulfinyl methane, propane-2-thiol, 3,5-dimethyl-1,2,4-trithiolane and 2-methyl-4-propyl-1,3-oxathiane as feed additives for all animal species

(Text with EEA relevance)

THE EUROPEAN COMMISSION,

Having regard to the Treaty on the Functioning of the European Union,

Having regard to Regulation (EC) No 1831/2003 of the European Parliament and of the Council of 22 September 2003 on additives for use in animal nutrition (1), and in particular Article 9(2) thereof,

Whereas:

(1)

Regulation (EC) No 1831/2003 provides for the authorisation of additives for use in animal nutrition and for the grounds and procedures for granting such authorisation. Article 10 of that Regulation provides for the re-evaluation of additives authorised pursuant to Council Directive 70/524/EEC (2).

(2)

3-(Methylthio) propionaldehyde, methyl 3-(methylthio) propionate, allylthiol, dimethyl sulfide, dibutyl sulfide, diallyl disulfide, diallyl trisulfide, dimethyl trisulfide, dipropyl disulfide, allyl isothiocyanate, dimethyl disulfide, 2-methylbenzene-1-thiol, S-methyl butanethioate, allyl methyl disulfide, 3-(methylthio) propan-1-ol, 3-(methylthio) hexan-1-ol, 1-propane-1-thiol, diallyl sulfide, 2,4-dithiapentane, 2-methyl-2-(methyldithio) propanal, 2-methylpropane-1-thiol, methylsulfinyl methane, propane-2-thiol, 3,5-dimethyl-1,2,4-trithiolane and 2-methyl-4-propyl-1,3-oxathiane (‘the substances concerned’) were authorised without a time limit in accordance with Directive 70/524/EEC as feed additives for all animal species. Those products were subsequently entered in the Register of feed additives as existing products, in accordance with Article 10(1) of Regulation (EC) No 1831/2003.

(3)

In accordance with Article 10(2) of Regulation (EC) No 1831/2003 in conjunction with Article 7 thereof, an application was submitted for the re-evaluation of the substances concerned as feed additives for all animal species. The applicant requested those additives to be classified in the additive category ‘sensory additives’. That application was accompanied by the particulars and documents required under Article 7(3) of Regulation (EC) No 1831/2003.

(4)

The European Food Safety Authority (‘the Authority’) concluded in its opinion of 17 April 2013 (3) that, under the proposed conditions of use in feed the substances concerned do not have adverse effects on animal health, human health or the environment. For allyl isothiocyanate, the Authority stated that, although additional exposure to that substance through its low use level in animal feeds would not substantially increase consumer exposure, the estimated exposure of consumers is already higher than the acceptable daily intake. For allyl isothiocyanate and 2-methylpropane-1-thiol maximum contents should be set up to ensure consumer safety and environmental protection, respectively. The Authority further concluded that the function of the substances concerned in feed is similar to that on food. The Authority has already concluded that for food the substances concerned are efficacious, as it increases the food smell or palatability. Therefore, that conclusion can be extrapolated for feed. The Authority could not conclude on the safety of the substances concerned used in water for drinking. However, those substances can be used within compound feeds which are subsequently administered via water.

(5)

Restrictions and conditions should be provided for to allow better control. For all the substances except allyl isothiocyanate and 2-methylpropane-1-thiol, since safety reasons do not require the setting of a maximum content and, taking into account the re-evaluation performed by the Authority, recommended contents should be indicated on the label of the additive. Where such contents are exceeded, certain information should be indicated on the label of premixtures, compound feeds and feed materials.

(6)

The Authority concluded that the substances concerned are to be considered as being irritant to skin, eyes and respiratory tract and as a skin sensitiser. Consequently, appropriate protective measures should be taken. The Authority does not consider that there is a need for specific requirements of post-market monitoring. It also verified the report on the method of analysis of the feed additives in feed submitted by the Reference Laboratory set up by Regulation (EC) No 1831/2003.

(7)

The assessment of the substances concerned shows that the conditions for authorisation, as provided for in Article 5 of Regulation (EC) No 1831/2003, are satisfied. Accordingly, the use of those substances should be authorised as specified in the Annex to this Regulation.

(8)

Since safety reasons do not require the immediate application of the modifications to the conditions of authorisation for the substances concerned, it is appropriate to allow a transitional period for interested parties to prepare themselves to meet the new requirements resulting from the authorisation.

(9)

The measures provided for in this Regulation are in accordance with the opinion of the Standing Committee on Plants, Animals, Food and Feed,

HAS ADOPTED THIS REGULATION:

Article 1

Authorisation

The substances specified in the Annex, belonging to the additive category ‘sensory additives’ and to the functional group ‘flavouring compounds’, are authorised as feed additives in animal nutrition subject to the conditions laid down in that Annex.

Article 2

Transitional measures

1.   The substances specified in the Annex and premixtures containing those substances, which are produced and labelled before 6 August 2017 in accordance with the rules applicable before 6 February 2017 may continue to be placed on the market and used until the existing stocks are exhausted.

2.   Compound feed and feed materials containing the substances as specified in the Annex which are produced and labelled before 6 February 2018 in accordance with the rules applicable before 6 February 2017 may continue to be placed on the market and used until the existing stocks are exhausted if they are intended for food-producing animals.

3.   Compound feed and feed materials containing the substances as specified in the Annex which are produced and labelled before 6 February 2019 in accordance with the rules applicable before 6 February 2017 may continue to be placed on the market and used until the existing stocks are exhausted if they are intended for non-food-producing animals.

Article 3

Entry into force

This Regulation shall enter into force on the twentieth day following that of its publication in the Official Journal of the European Union.

This Regulation shall be binding in its entirety and directly applicable in all Member States.

Done at Brussels, 14 December 2016.

For the Commission

The President

Jean-Claude JUNCKER


(1)OJ L 268, 18.10.2003, p. 29.

(2)  Council Directive 70/524/EEC of 23 November 1970 concerning additives in feeding-stuffs (OJ L 270, 14.12.1970, p. 1).

(3)  EFSA Journal 2013;11(5):3208.


ANNEX

Identification number of the additive

Name of the holder of authorisation

Additive

Composition, chemical formula, description, analytical method

Species or category of animal

Maximum age

Minimum content

Maximum content

Other provisions

End of period of authorisation

mg of active substance/kg of complete feedingstuff with a moisture content of 12 %

(1)

(2)

(3)

(4)

(5)

(6)

(7)

(8)

(9)

Category: Sensory additives. Functional group: Flavouring compounds

2b12001

3-(Methylthio)propionaldehyde

Additive composition

3-(Methylthio) propionaldehyde

Characterisation of the active substance

3-(Methylthio) propionaldehyde

Produced by chemical synthesis

Purity: min. 98 %

Chemical formula: C4H8OS

CAS number 3268-49-3

FLAVIS No 12.001

Method of analysis (1)

For the determination of 3-(methylthio) propionaldehyde in the feed additive and in feed flavouring premixtures:

Gas chromatography mass spectrometry with retention time locking GC-MS-RTL.

All animal species

1.

The additive shall be incorporated into the feed in the form of a premixture.

2.

In the directions for use of the additive and premixtures, the storage and stability conditions shall be indicated.

3.

The recommended maximum content of the active substance shall be: 0,05 mg/kg of complete feedingstuff with a moisture content of 12 %.

4.

On the label of the additive the following shall be indicated:

‘Recommended maximum content of the active substance of complete feedingstuff with a moisture content of 12 %: 0,05 mg/kg’.

5.

The functional group, the identification number, the name and the added amount of the active substance shall be indicated on the labelling of the premixtures, feed materials and compound feedingstuffs, if the following content of the active substance in complete feedingstuff with a moisture content of 12 % is exceeded: 0,05 mg/kg.

6.

For users of the additive and premixtures, feed business operators shall establish operational procedures and organisational measures to address potential risks by dermal contact or eyes contact. Where those risks cannot be eliminated or reduced to a minimum by such procedures and measures, the additive and premixtures shall be used with personal protective equipment, including safety glasses and gloves.

6 February 2027

2b12002

Methyl 3-(methylthio)propionate

Additive composition

Methyl 3-(methylthio)propionate

Characterisation of the active substance

Methyl 3-(methylthio)propionate

Produced by chemical synthesis

Purity: min. 97 %

Chemical formula: C5H10O2S

CAS number 13532-18-8

FLAVIS No 12.002

Method of analysis (1)

For the determination of methyl 3-(methylthio)propionate in the feed additive and in feed flavouring premixtures:

Gas chromatography mass spectrometry with retention time locking GC-MS-RTL.

All animal species

1.

The additive shall be incorporated into the feed in the form of a premixture.

2.

In the directions for use of the additive and premixtures, the storage and stability conditions shall be indicated.

3.

The recommended maximum content of the active substance shall be: 0,05 mg/kg of complete feedingstuff with a moisture content of 12 %.

4.

On the label of the additive the following shall be indicated:

‘Recommended maximum content of the active substance of complete feedingstuff with a moisture content of 12 %: 0,05 mg/kg’.

5.

The functional group, the identification number, the name and the added amount of the active substance shall be indicated on the labelling of the premixtures, feed materials and compound feedingstuffs, if the following content of the active substance in complete feedingstuff with a moisture content of 12 % is exceeded: 0,05 mg/kg.

6.

For users of the additive and premixtures, feed business operators shall establish operational procedures and organisational measures to address potential risks by dermal contact or eyes contact. Where those risks cannot be eliminated or reduced to a minimum by such procedures and measures, the additive and premixtures shall be used with personal protective equipment, including safety glasses and gloves.

6 February 2027

2b12004

Allylthiol

Additive composition

Allylthiol

Characterisation of the active substance

Allylthiol

Produced by chemical synthesis

Purity: min. 75 % (min. 98 % allylthiol + allyl sulphide + allyl mercaptan)

Chemical formula: C3H6S

CAS number 870-23-5

FLAVIS No 12.004

Method of analysis (1)

For the determination of allylthiol in the feed additive and in feed flavouring premixtures:

Gas chromatography mass spectrometry with retention time locking GC-MS-RTL.

All animal species

Organic Chemistry Portal

Reactions > Organic Synthesis Search

Categories: S-S Bond Formation >

Synthesis of Trisulfides

Recent Literature


A straightforward preparation of 1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)trisulfanyl]dodecane from readily available substrates, followed by reaction with aliphatic and aromatic thiols enables the synthesis of unsymmetrical trisulfides under mild conditions in very good yields.
S. Lach, M. Sliwka-Kaszynska, D. Witt, Synlett, 2010, 2857-2860.


Convenient methods for the synthesis of symmetrical trisulfides from aliphatic and aromatic thiols under mild conditions are based on the straightforward preparation of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorin-2-yl)disulfanyl derivatives from readily available 5,5-dimethyl-2-sulfanyl-2-thioxo-1,3,2-dioxaphosphorinane or bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl) disulfide.
A. Kertmen, S. Lach, J. Rachon, D. Witt, Synthesis, 2009, 1459-1462.

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