generating AES 256 bit key value

Question 1

You can construct the Rfc2898DeriveBytes Class with an arbitrary sized password and then derive a key of your desired size in this case, 256 bits (32 bytes):

private static byte[] CreateKey(string password, int keyBytes = 32)
{
    const int Iterations = 300;
    var keyGenerator = new Rfc2898DeriveBytes(password, Salt, Iterations);
    return keyGenerator.GetBytes(keyBytes);
}

In order to produce a deterministic output (i.e. same input will produce the same output) you will need to hard-code the salt. The salt must be at least 8 bytes:

private static readonly byte[] Salt = 
    new byte[] { 10, 20, 30 , 40, 50, 60, 70, 80};

Question 2

Probably the best way is to use PBKDF2 using SHA256 (which will generate 256 bit output) and a application specific salt & iteration count. You should be aware that using an application specific salt removed quite a lot of the protection from PBKDF2, so you may require additional protection to alleviate this issue. One method would be to make sure that the database is safe, and that a maximum amount of tries can be used.

You are correct in stipulating that a 32 char passphrase is not a 256 bit key. It does not contain enough entropy, and some bytes may not even have valid character representations.

Question 3

public static string GenerateBitKey(int letterCount = 44)
    {
        // Get the number of words and letters per word.
        int num_letters = letterCount;
        // Make an array of the letters we will use.
        char[] letters = "ABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789".ToCharArray();

        // Make a random number generator.
        Random rand = new Random();

        // Make the words.
        // Make a word.
        string word = "";
        for (int j = 1; j <= num_letters; j++)
        {
            // Pick a random number between 0 and 25
            // to select a letter from the letters array.
            int letter_num = rand.Next(0, letters.Length - 1);

            // Append the letter.
            word += letters[letter_num];
        }
        return word;
    }

Question 4

 private static IBuffer GetMD5Hash(string key)
    {
        IBuffer bufferUTF8Msg = CryptographicBuffer.ConvertStringToBinary(key, BinaryStringEncoding.Utf8);
        HashAlgorithmProvider hashAlgorithmProvider = HashAlgorithmProvider.OpenAlgorithm(HashAlgorithmNames.Md5);
        IBuffer hashBuffer = hashAlgorithmProvider.HashData(bufferUTF8Msg);
        if (hashBuffer.Length != hashAlgorithmProvider.HashLength)
        {
            throw new Exception("There was an error creating the hash");
        }
        return hashBuffer;
    }

    #region Static

    public static string GenerateKey(string password, int resultKeyLength = 68)
    {
        if (password.Length < 6)
            throw new ArgumentException("password length must atleast 6 characters or above");
        string key = "";

        var hashKey = GetMD5Hash(password);
        var decryptBuffer = CryptographicBuffer.ConvertStringToBinary(password, BinaryStringEncoding.Utf8);
        var AES = SymmetricKeyAlgorithmProvider.OpenAlgorithm(SymmetricAlgorithmNames.AesEcbPkcs7);
        var symmetricKey = AES.CreateSymmetricKey(hashKey);
        var encryptedBuffer = CryptographicEngine.Encrypt(symmetricKey, decryptBuffer, null);
        key = CryptographicBuffer.EncodeToBase64String(encryptedBuffer);
        string cleanKey  = key.Trim(new char[] { ' ', '\r', '\t', '\n', '/', '+', '=' });
        cleanKey = cleanKey.Replace("/", string.Empty).Replace("+", string.Empty).Replace("=", string.Empty);
        key = cleanKey;
        if(key.Length > resultKeyLength)
        {
           key = key.Substring(0, Math.Min(key.Length, resultKeyLength));
        }
        else if(key.Length == resultKeyLength)
        {
            return key;
        }
        else if (key.Length < resultKeyLength)
        {
            key = GenerateKey(key);
        }
        return key;

    }

//Get the first 44 charaters for the AES Key and the remaining chars for AES IV

Question 5

You can use some hash function that provides 256 bit outuput from input of any length, for example SHA256.

Question 6

My version. I just wanted keys without a password.

    public static string GenerateBitKey(int letterCount = 44)
    {
        // Get the number of words and letters per word.
        int num_letters = letterCount;
        // Make an array of the letters we will use.
        char[] letters = "ABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789abcdefghijklmnopqrsruvwxyz+".ToCharArray();
        int lettersLength =  letters.Length;

        // Make a word.
        string word = "";

        //Use Cryptography to generate random numbers rather than Psuedo Random Rand
        // Deliberate overkill here
        byte[] randomBytes = new byte[num_letters*256];


        List<int> rands = new List<int>();
        do
        {
            using (System.Security.Cryptography.RNGCryptoServiceProvider rngCsp = new
                        System.Security.Cryptography.RNGCryptoServiceProvider())
            {
                // Fill the array with a random value.
                rngCsp.GetBytes(randomBytes);
            }


            // Truncate the set of random bytes to being in range 0 .. (lettersLength-1)
            // Nb Using mod of randomBytes will reduce entropy of the set

            foreach (var x in randomBytes)
            {
                if (x < lettersLength)
                    rands.Add((int)x);
                if (rands.Count()==num_letters)
                     break;
            }
        }
        while (rands.Count < letterCount);


        int[] randsArray = rands.ToArray();

        // Get random selection of characters from letters
        for (int j = 0; j < num_letters; j++)
        {
            int letter_num = randsArray[j];
            // Append the letter.
            word += letters[letter_num];
        }
        return word;
    }