Classifications

• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0069—Heterocyclic compounds
  • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0069—Heterocyclic compounds
  • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
  • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms

Definitions

• the present invention primarily relates to a method for producing a particulate product comprising or consisting of the steps as described herein.
• the invention further relates to a particulate product, preferably obtained or obtainable by a method as described herein, comprising 70 to 98 wt.-% compound of formula (la) as defined herein and 0.01 to 5 wt.-% compound of formula (Ib) as defined herein, and to the use of a particulate product as described herein as a fragrance.
• Ambrocenide ® a powerful fragrance substance with an ambery and woody scent, has the following chemical structure (formula A):
• Ambrocenide ® may generally comprise one, two, three or all of the following diastereomers (formula B):
• Ambrocenide ® is disclosed in EP 0 857 723 B1 .
• (-)-alpha-cedrene (1) is converted to (-)-alpha cedrene epoxide (2) by treatment with peracetic acid.
• the epoxide obtained (2) is then converted into a mixture of the epimeric cedrane diols (3) by acid catalysed ring opening.
• the crude Ambrocenide ® obtained from synthesis may comprise one, two, three or all of the diastereomers shown in formula B above.
• WO 2017/186973 A2 describes a method for manufacturing a mixture comprising the compound of formula (Ia)
• Ambrocenide ® has been marketed by the applicant in two different qualities.
• One of the qualities is so-called Ambrocenide ® Cryst., a highly pure crystalline solid (> 99% GC area of the compound of formula (la) as defined herein), which is manufactured via an effortful solvent recrystallization of the amorphous crude Ambrocenide ® obtained from synthesis. This purification method is associated with significant yield losses and hence substantial manufacturing costs.
• An alternative quality supplied by the applicant is so-called Ambrocenide ® 10 DPG, which is a 10% solution of the amorphous crude Ambrocenide ® obtained from synthesis in dipropylene glycol (DPG).
• the stated object is surprisingly achieved by a method for producing a particulate product comprising or consisting of the following steps:
• step (iii) of the method according to the invention (at a temperature as defined below) can be brought to solidification within only a few seconds.
• step (vi) of the method according to the invention advantageously exhibits an almost identical X-ray powder diffraction pattern to the one of the highly pure compound Ambrocenide ® Cryst. (> 99% GC area of the compound of formula (la) as defined herein; cf. Figure 1 and Example 2 below).
• the mixture, preferably unpurified synthesis product, provided in step (i), and accordingly the vapor-treated, partially or fully molten mass obtained in step (iii) of the method according to the invention comprises only 70 to 98 wt.-% of the compound of formula (la) and a further five to seven minor components, which are the compound of formula (Ib) and educts and side-products from synthesis (cf. further below for details).
• step (vi) of the method according to the invention The high crystallinity of the particulate product obtained in step (vi) of the method according to the invention was thus very surprising, especially considering the amorphous nature of the mixture, preferably unpurified synthesis product, provided in step (i) of the method according to the invention at room temperature and the absence of any purification steps, which would be capable of removing any remaining educts and side-products from synthesis, in the method according to the invention. Moreover, when samples of Ambrocenide ® Cryst.
• the method according to the invention thus advantageously gives access to a particulate product as defined herein, i.e. to a particulate form of Ambrocenide ® , which is easy to produce and convenient to handle due to its solid, particulate, and crystalline form, and which has almost identical crystallinity and olfactive properties as the highly purified product Ambrocenide ® Cryst. with > 99% GC area of compound of formula (Ia) as defined herein (cf. Figure 1 and Examples 2 and 3 below).
• an unpurified synthesis product relates to a product obtained from chemical synthesis (e.g. as described below in Example 1), which may have been washed after synthesis, but which has not been subjected to any purification procedures such as fractional distillation or recrystallization.
• the mixture provided in step (i) comprises or consists of 70 to 98 wt.-% of compound of formula (la) and 0.01 to 5 wt.-% of compound of formula (Ib), based on the total weight of the mixture.
• the mixture provided in step (i) comprises or consists of 80 to 96 wt.-% of compound of formula (la) and 0.01 to 1 wt.-% of compound of formula (Ib), based on the total weight of the mixture.
• the mixture provided in step (i) comprises or consists of 80 to 95 wt.-% of compound of formula (la) and 0.01 to 1 wt.-% of compound of formula (Ib), based on the total weight of the mixture.
• the mixture provided in step (i) is at an average temperature of from 35 to 85 °C, preferably from 55 to 85 °C, most preferably from 80 to 85°C. Providing the mixture at this temperature is particularly advantageous, because it then is in the form of a partially or fully molten mass.
• the mixture preferably the unpurified synthesis product
• the mixture is provided at a temperature that is sufficiently high for the mixture to be in the form of a fully molten mass, i.e. a mass that is essentially free from any solid form of the mixture, preferably unpurified synthesis product, in step (i).
• the mixture, preferably unpurified synthesis product is provided at a temperature for the mixture, preferably unpurified synthesis product, to be in the form of a partially molten mass, i.e. a mass that contains a solid form of the mixture, preferably unpurified synthesis product, in step (i).
• the partially molten mass provided may, for example, contain from more than 0 to 65 wt.%, preferably more than 0 to 10 wt.%, most preferably more than 0 to 2 wt.% of solid mixture, preferably unpurified synthesis product.
• the partially or fully molten mass contacted with a solvent having a boiling point that is lower than the boiling point of said mass, preferably with water, in step (iii) of the method according to the invention is at an average temperature of from 35 to 85°C, preferably from 55 to 85 °C, most preferably from 80 to 85 °C, when first contacting the solvent.
• the mixture, preferably the (amorphous) unpurified synthesis product, provided in step (i) of the method according to the invention is subjected to a vapor, preferably steam, treatment in step (iii) of the method according to the invention.
• Said vapor, preferably steam, treatment advantageously removes unpleasant and/or undesired olfactory notes from the mixture, preferably unpurified synthesis product, caused e.g. by remaining (low boiling) solvent residues from the synthesis of the mixture, preferably unpurified synthesis product.
• the vessel holding the partially or fully molten mass in step (iii) of the method according to the invention is held at a temperature that is high enough for the partially or fully molten mass not to solidify during the contacting with the solvent.
• the solvent used in step (iii) of the method according to the invention is water, more preferably is tap water.
• the solvent more preferably the water, is at room temperature when first contacting the partially or fully molten mass in step (iii) of the method according to the invention.
• step (iii) of the method according to the invention after the contacting of the partially or fully molten mass with the solvent, preferably water, the pressure and temperature inside the vessel are adjusted to 7 - 1013 mbar and 30 - 100 °C, preferably to 60 - 500 mbar and 60 - 90°C, more preferably to 125 - 250 mbar and 70 - 80 °C.
• the solvent preferably the water
• the solvent is evaporated again from the mass (if added in liquid state) or is removed again from the mass (if added in gaseous state).
• the amount of solvent, preferably water, used per vapour, preferably steam, treatment of the partially or fully molten mass preferably is 5 to 400 wt.-%, more preferably 5 to 300 wt.-%, more preferably 5 to 200 wt.-%, more preferably 5 to 100 wt.-%, more preferably 10 to 50 wt.-%, most preferably 20 to 25 wt.-%, of the weight of the molten mass treated in step (iii) of the method according to the invention.
• the vapour, preferably steam, treatment of step (iii) of the method according to the invention may be repeated once to ten times, preferably twice to five times, most preferably three to four times.
• step (i) it advantageously removes low boiling organic solvents from the partially or fully molten mass provided in step (i), if applicable, or obtained in step (ii), which may still be present in the mixture as provided in step (i) from synthesis. However, it is not capable of removing any educts and side-products from synthesis due to their higher boiling points.
• step (iv) of the method according to the invention the contacting of the vapor, preferably steam, treated partially or fully molten mass obtained in step (iii) of the method with a cold surface takes place over a period of 2 to 60 seconds, preferably 4 to 40 seconds, particularly preferably 5 to 25 seconds.
• the vapor, preferably steam, treated partially or fully molten mass obtained in step (iii) and contacted with a cold surface in step (iv) of the method according to the invention does not comprise any solvents, more preferably does not comprise any organic solvents, most preferably is essentially free of organic solvents, after the vapor treatment of step (iii).
• the vapor, preferably steam, treated partially or fully molten mass obtained in step (iii) of the method according to the invention is not a solution of the mixture, preferably unpurified synthesis product, as provided in step (i) of the method in one or more solvents.
• the total amount of solids, in wt.-%, based on the total weight of the partially molten mass, contained in a partially molten mass provided in step (i) and/or obtained in step (ii), if applicable, and/or obtained in step (iii) and/or contacted with a cold surface in step (iv) of the method according to the invention is from more than 0 to 65 wt.-%, preferably more than 0 to 10 wt.-%, most preferably more than 0 to 2 wt.-%.
• the method according to the invention does not comprise any fractional distillation and/or recrystallization steps.
• the solid product that is in contact with the cold surface which is obtained in step (v) of the method according to the invention, comprises or consists of essentially the same amount of compound of formula (la) and compound of formula (Ib), in percentage terms, as defined above for the mixture provided in step (i) of the method.
• the solid product obtained in step (v) comprises or consists of 70 to 98 wt.-% of compound of formula (la) and 0.01 to 5 wt.-% of compound of formula (Ib), based on the total weight of the solid product.
• the solid product obtained in step (v) comprises or consists of 80 to 96 wt.-% of compound of formula (la) and 0.01 to 1 wt.-% of compound of formula (Ib), based on the total weight of the solid product.
• the solid product obtained in step (v) comprises or consists of 80 to 95 wt.-% of compound of formula (la) and 0.01 to 1 wt.-% of compound of formula (Ib), based on the total weight of the solid product.
• solid has the usual meaning in the field of natural sciences.
• the molecules in a solid are closely packed together and contain the least amount of kinetic energy.
• a solid is characterized by structural rigidity and resistance to a force applied to the surface. Unlike a liquid, a solid object does not flow to take on the shape of its container, nor does it expand to fill the entire available volume like a gas.
• the blade preferably the (discharge) knife, used to remove of the solid product from the cold surface in step (vi) is used at an angle of 10 to 70°, preferably 20 to 65°, more preferably 30° to 60°, relative to the surface of the solid product.
• the removal of the solid product from the cold surface to obtain a particulate product in step (vi) is performed by scraping the solid product off the cold surface, preferably with a blade, more preferably with a (discharge) knife.
• step (vi) of the method according to the invention no further crushing steps and/or other size changes of the obtained particulate product is/are carried out.
• the particulate product obtained in step (vi) of the method according to the invention comprises or consists of essentially the same amount of compound of formula (Ia) and compound of formula (Ib), in percentage terms, as defined above for the mixture provided in step (i) of the method and for the solid product obtained in step (v).
• the particulate product obtained in step (vi) comprises or consists of 70 to 98 wt.-% of compound of formula (la) and 0.01 to 5 wt.-% of compound of formula (Ib), based on the total weight of the particulate product.
• the particulate product obtained in step (vi) comprises or consists of 80 to 96 wt.-% of compound of formula (la) and 0.01 to 1 wt.-% of compound of formula (Ib), based on the total weight of the particulate product.
• the particulate product obtained in step (vi) comprises or consists of 80 to 95 wt.-% of compound of formula (la) and 0.01 to 1 wt.-% of compound of formula (Ib), based on the total weight of the particulate product.
• the mixture, preferably unpurified synthesis product, provided in step (i) of the method according to the invention further comprises one or several compound(s) of formula (II)
• the solid product obtained in step (v) of the method according to the invention further comprises one or several compound(s) of formula (II)
• the particulate product obtained in step (vi) of the method according to the invention further comprises one or several compound(s) of formula (II)
• the mixture, preferably unpurified synthesis product, provided in step (i) of the method according to the invention further comprises comprises one or several compound(s) of formula (II),
• the solid product obtained in step (v) of the method according to the invention further comprises comprises one or several compound(s) of formula (II),
• the particulate product obtained in step (vi) of the method according to the invention further comprises comprises one or several compound(s) of formula (II),
• the particulate product obtained in step (vi) is crystalline.
• the mixture, preferably unpurified synthesis product, provided in step (i) is heated to an average temperature of from 35 to 85 °C, preferably from 55 to 85 °C, most preferably from 80 to 85 °C, in step (ii), if present.
• the mixture, preferably the unpurified synthesis product, provided in step (i) is heated in step (ii), if present, to a sufficiently high temperature to obtain a fully molten mass, i.e. a mass that is essentially free from any solid form of the mixture, preferably unpurified synthesis product.
• the mixture, preferably unpurified synthesis product, provided in step (i) is only heated to a temperature that leads to partial melting of the mixture, preferably unpurified synthesis product, i.e. to a partially molten mass, in step (ii), if present.
• the partially molten mass obtained may, for example, contain from more than 0 to 65 wt.%, preferably more than 0 to 10 wt.%, most preferably more than 0 to 2 wt.% of solid mixture, preferably unpurified synthesis product.
• the vapor-treated, partially or fully molten mass obtained in step (iii) is at an average temperature of from 35 to 85 °C, preferably from 55 to 85 °C, most preferably from 80 to 85 °C, when first contacting the cold surface in step (iv).
• the cold surface with which the vapor-treated, partially or fully molten mass obtained in step (iii) is contacted in step (iv) has an average (essentially constant) temperature of from 0 to 25 °C, more preferably from 0 to 20 °C, more preferably from 5 to 15 °C, most preferably from 8 to 12 °C (especially when first contacting the partially or fully molten mass in step (iv) of the method according to the invention).
• the cold surface with which the vapor-treated, partially or fully molten mass obtained in step (iii) is contacted in step (iv) of the method is constantly kept at an average temperature of from 0 to 25 °C, more preferably from 0 to 20 °C, more preferably from 5 to 15 °C, most preferably from 8 to 12 °C, by way of cooling means.
• the vapor-treated, partially or fully molten mass is cooled - preferably through the contact with the cold surface - to an average temperature of from 0 to 25 °C, more preferably from 0 to 20 °C, more preferably from 5 to 15 °C, most preferably from 8 to 12 °C.
• the solid product obtained in step (v) of the method according to the invention is crystalline.
• the particulate product obtained in step (vi) is in the form of flakes.
• a particle of the particulate product, more preferably a flake, obtained in step (vi) of the method according to the invention has a length of from 1 to 50 mm, preferably from 2 to 40 mm, more preferably from 5 to 30 mm, and/or a width of from 0.5 to 30 mm, preferably from 2 to 20 mm, more preferably from 3 to 10 mm, and/or a thickness of from 0.1 to 5 mm, preferably from 0.5 to 3 mm, more preferably from 1 to 2 mm.
• a particle of the particulate product, more preferably a flake, obtained in step (vi) of the method according to the invention has a length of from 1 to 50 mm, preferably from 2 to 40 mm, more preferably from 5 to 30 mm, and a width of from 0.5 to 30 mm, preferably from 2 to 20 mm, more preferably from 3 to 10 mm, and a thickness of from 0.1 to 5 mm, preferably from 0.5 to 3 mm, more preferably from 1 to 2 mm.
• the particles of the particulate product, preferably the flakes, obtained in step (vi) of the method according to the invention are elongated and/or needle-like.
• the size and/or shape of the particles of the particulate product can be influenced by the kind of blade, preferably (discharge) knife, used in step (vi) of the method according to the invention and/or by the removal angle set for the blade, preferably (discharge) knife.
• the contacting of the vapor-treated, partially or fully molten mass obtained in step (iii) with the cold surface in step (iv) of the method according to the invention comprises or consists of the following step: Partially or fully submerging the cold surface in the molten mass followed by removal of the cold surface from the molten mass to form a layer of the molten mass on at least parts of the cold surface.
• residual seed crystals of the particulate product from a previous application of the method according to the invention are still present on the cold surface. This is particularly advantageous, since it facilitates the formation of the solid product (preferably in crystalline form) on the cold surface.
• the cold surface is the outer surface of a cooling roll that rotates while parts of its outer surface (e.g. its top or bottom outer surface) are in contact with the molten mass.
• the cold surface is the outer surface of a cooling roll that rotates while the molten mass is poured onto it. In both cases, a thin layer of the molten mass is deposited on and adheres to the outer surface of the rotating cooling roll in a continuous process. Since the average temperature of the outer surface of the cooling roll is lower than the average temperature of the molten mass, preferably is below the crystallization temperature of the molten mass, a layer of the solid product is formed on the outer surface of the cooling roll.
• the solid product is removed from its surface, for example by a blade, preferably a (discharge) knife, scraper. Thereby, the solid product is comminuted to the particulate product, which may be in the form of flakes (cf. Figures 2 and 3 ).
• the rotation speed of the cooling roll is 0.5 to 12 rpm, more preferably 1 to 8 rpm, most preferably 2 to 4 rpm. If the rotation speed of the cooling roll is too slow, the space-time-yield of the particulate product obtained in step (vi) can be unsatisfactory. If the rotation speed of the cooling roll is too fast, the molten mass may not have enough time to cool down and solidify and an undesired waxy mass may be obtained in step (v) of the method instead of a solid product.
• the molten mass is in contact with the cold surface for a time of from 2 to 60 seconds, preferably from 4 to 40 seconds, more preferably from 5 to 25 seconds.
• the cooling time in step (v) of the method according to the invention preferably is from 2 to 60 seconds, more preferably from 4 to 40 seconds, most preferably from 5 to 25 seconds.
• a drum flaker can be used in the method according to the invention.
• the layer of the molten mass, formed on the cold surface by contacting the vapor-treated, partially or fully molten mass with the cold surface in step (iv) of the method according to the invention has an average thickness of from 0.1 to 5 mm, more preferably 0.5 to 3 mm, most preferably 1 to 2 mm.
• the cold surface with which the vapor-treated, partially or fully molten mass obtained in step (iii) is contacted in step (iv) of the method is the upper surface of a cooling belt that rotates while the molten mass is poured onto it. Since the average temperature of the cooling belt preferably is adjusted to be lower than the average temperature of the molten mass, preferably is adjusted to be below the crystallization temperature of the molten mass, a layer of the solid product is formed on the upper surface of the cooling belt in step (v) of the method according to the invention.
• the cold surface with which the vapor-treated, partially or fully molten mass obtained in step (iii) is contacted in step (iv) of the method is the upper surface of a lower cooling belt that rotates while the molten mass is poured onto it. Then, the molten mass on the lower cooling belt is also contacted with lower surface of an upper cooling belt from the top.
• the average temperature of one or both of the lower and upper cooling belt(s), which are then both in contact with the molten mass is adjusted to be lower than the average temperature of the molten mass, preferably is adjusted to be below the crystallization temperature of the molten mass, a layer of the solid product is formed on the surface of one or both of the lower and upper cooling belt(s) in step (v) of the method according to the invention.
• the particulate product obtained in step (vi) is in the form of pastilles.
• the particulate product, preferably the pastilles, obtained in step (vi) of the method according to the invention have an average diameter of from 2 to 12 mm, more preferably 3 to 10 mm, most preferably 4 to 8 mm (top view), and/or average height of from 1 to 10 mm, more preferably 2 to 8 mm, most preferably 3 to 6 mm (side view).
• the contacting of the vapor-treated, partially or fully molten mass obtained in step (iii) with the cold surface in step (iv) comprises or consists of the following step: Depositing the molten mass on the cold surface to form one or more separate droplets of the molten mass on the cold surface.
• the formed droplets of the molten mass on the cold surface have an average diameter of from 2 to 12 mm, more preferably 3 to 10 mm, most preferably 4 to 8 mm (top view) and/or have an average height of from 1 to 10 mm, more preferably 2 to 8 mm, most preferably 3 to 6 mm (side view).
• step (vi) of the method according to the invention makes the solid product, and respectively, the particulate product obtainable in the form of pastilles.
• the cold surface that the vapor-treated, partially or fully molten mass obtained in step (iii) is contacted with in step (iv) of the method according to the invention is the outer surface of a (rotatable) cooling roll (cf. Figure 2 ).
• the cold surface that the vapor-treated, partially or fully molten mass obtained in step (iii) is contacted with in step (iv) of the method according to the invention is the outer surface of a cooling roll having a maximum diameter of about 2000 mm, more preferably of about 1500 mm, more preferably of about 1000 mm, most preferably of about 500 mm.
• the cold surface that the vapor-treated, partially or fully molten mass obtained in step (iii) is contacted with in step (iv) of the method is the upper or lower surface of a (rotatable) cooling belt.
• the cold surface that the vapor-treated, partially or fully molten mass obtained in step (iii) is contacted with in step (iv) of the method according to the invention has a roughness of 0.1 to 2 ⁇ m, preferably of 0.4 to 0.8 ⁇ m.
• Another aspect of the present invention relates to a particulate product, preferably obtained or obtainable by a method according to the invention as described herein, comprising 70 to 98 wt.-% preferably 80 to 96 wt.-%, more preferably 80 to 95 wt.-%, compound of formula (la)
• the product comprises or consists of 70 to 98 wt.-% of compound of formula (la) and 0.01 to 5 wt.-% of compound of formula (Ib), based on the total weight of the product.
• the product comprises or consists of 80 to 96 wt.-% of compound of formula (la) and 0.01 to 1 wt.-% of compound of formula (Ib), based on the total weight of the product.
• the product comprises or consists of 80 to 95 wt.-% of compound of formula (la) and 0.01 to 1 wt.-% of compound of formula (Ib), based on the total weight of the product.
• the product further comprises one or several compound(s) of formula (II)
• the particulate product further comprises one or several compound(s) of formula (II),
• the particulate product according to the invention is in the form of flakes.
• a particle of the particulate product more preferably a flake, according to the invention has a length of from 1 to 50 mm, preferably from 2 to 40 mm, more preferably from 5 to 30 cm, and/or a width of from 0.5 to 30 mm, preferably from 2 to 20 mm, more preferably from 3 to 10 mm, and/or a thickness of from 0.1 to 5 mm, preferably from 0.5 to 3 mm, more preferably from 1 to 2 mm.
• a particle of the particulate product more preferably a flake, according to the invention has a length of from 1 to 50 mm, preferably from 2 to 40 mm, more preferably from 5 to 30 cm, and a width of from 0.5 to 30 mm, preferably from 2 to 20 mm, more preferably from 3 to 10 mm, and a thickness of from 0.1 to 5 mm, preferably from 0.5 to 3 mm, more preferably from 1 to 2 mm.
• the particles of the particulate product, preferably the flakes, according to the invention have an average length of from 5 to 30 mm, and/or an average width of from 3 to 10 mm, and/or an average thickness of from 1 to 2 mm.
• the particles of the particulate product, preferably the flakes, according to the invention have an average length of from 5 to 30 mm, and an average width of from 3 to 10 mm, and an average thickness of from 1 to 2 mm.
• the particles of the particulate product, preferably the flakes, according to the invention are elongated and/or needle-like.
• the particulate product according to the invention is in the form of pastilles.
• the particulate product preferably the pastilles, according to the invention have an average diameter of from 2 to 12 mm, more preferably 3 to 10 mm, most preferably 4 to 8 mm (top view), and/or average height of from 1 to 10 mm, more preferably 2 to 8 mm, most preferably 3 to 6 mm (side view).
• the particulate product according to the invention is particularly advantageous as it is easy and convenient to handle for consumers, such as perfumers, due to its solid, particulate and crystalline form. Due to the method according to the invention (as described above), it is more easily accessible than Ambrocenide ® Cryst., a highly pure crystalline solid with > 99% GC area of the compound of formula (Ia) as defined herein, which is manufactured via an effortful solvent recrystallization of the amorphous crude Ambrocenide ® obtained from synthesis, while displaying essentially identical olfactive properties to Ambrocenide ® Cryst. (cf. Examples 3 to 9 below).
• Another aspect of the present invention relates to the use of a particulate product according to the invention as a fragrance, in particular for the preparation of a perfume oil.
• the particulate product according to the invention is used as a fragrance for imparting, modifying and/or enhancing one or more odour notes selected from the group consisting of ambery, wood, and amber.
• Example 1 Preparation of a mixture comprising the compound of formula (la) and the compound of formula (Ib) (as provided in step (i) of the method according to the invention)
• reaction described above can be scaled up accordingly for production of the starting mixture on a larger scale, as required.
• a solution consisting of 53 kg of acetone and 0.167 kg of technical sulphuric acid is then added at a temperature of not more than 30 °C for a period of 2 hours. After a further stirring time of 4 hours, the reaction mixture is adjusted to a pH of at least 8 with a slurry consisting of 1.6 kg of calcined soda in 5 kg of water.
• the low boilers are removed from the reaction mixture to such an extent that a sump temperature of 95 °C is not exceeded.
• 38 kg of methyl-tert.-butyl ether are added to the distillation residue and stirred at a temperature of about 35 °C for about 30 minutes.
• the reaction mixture is then left to rest until a clear two-phase mixture is obtained.
• the aqueous phase is separated off and 12 kg of water are added to the remaining organic phase.
• the mixture obtained is stirred at a temperature of about 35 °C for about 30 minutes.
• the reaction mixture is then left to rest until a clear two-phase mixture is obtained.
• the aqueous phase is separated off and methyl-tert.-butyl ether is removed during subsequent distillation of the organic phase, to such an extent that a sump temperature of 95 °C is not exceeded at 40 mbar, to obtain an unpurified synthesis product in the form of a fully molten mass.
• Water is added to the fully molten mass, which leads to a sump temperature of 70 °C at 1013 mbar.
• the evaporation of the water is performed by increasing the sump temperature up to 95°C and simultaneously lowering the pressure down to 40 mbar.
• the obtained (water) vapor-treated fully molten mass comprises 89.2 wt.-% of compound of formula (la) and 0.13 wt.-% of compound of formula (Ib) as defined herein:

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• 2023
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